# Anna Maria Island Rentals With a Pool, Island Vacation Properties

Updated: 2026-11-13

Our Anna Maria Island rentals with a pool allow you to hop into the water whenever you please on your next trip to Florida! You'll have plenty of space to entertain your family both indoors and out, and you'll never be more than a few minutes from the best Anna Maria Island attractions. Inside our Anna Maria Island rentals, you'll find a whole host of incredible features and amenities.

Book Your Anna Maria Island Rental with a Pool Today!

By staying in one of our Anna Maria Island rentals with a private pool, you’ll be just a quick walk, bike, or trolley ride away from any activity you might want to experience! Head to local beaches like Manatee Public Beach or Coquina Beach for a fun afternoon with your family or get your souvenir shopping done on Pine Avenue or Historic Bridge Street. Learn about the area’s history at the Anna Maria Historical Society, have a delicious meal at the Rod and Reel Pier, or simply spend your days strolling down the streets. The possibilities are endless!

Our Anna Maria Island Vacation Rentals

Island Vacation Properties is proud to be your premier resource for luxurious yet affordable Anna Maria Island rentals. Our team is full of local professionals who know all about the area and can help you find the perfect vacation rental for you and your family. If you’ve got a specific budget in mind, if you know exactly which neighborhood you want to stay in, or if you’re going to be near a particular attraction, we can make it happen! Contact us today to learn more about all of our Anna Maria Island vacation rentals!

## Rentals in this collection (121)

Live price for dates: add ?arr=YYYY-MM-DD&dep=YYYY-MM-DD&people=N to any property page.
(arr = check-in date, dep = checkout date, people = number of guests)
Rating = guest rating out of 5 (number of reviews).

| Property | Location | Bedrooms | Sleeps | Pets | Rating | Page | Data |
|---|---|---|---|---|---|---|---|
| The Point at Bermuda Bay Club | Bradenton Beach, FL | 3 | 6 | No | 5 (24) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-250437/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-250437.md) |
| 1239 Edgewater Circle | Bradenton, FL | 2 | 4 | No | 4 (1) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-241210/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-241210.md) |
| Absolutely Perfect | Holmes Beach, FL | 4 | 8 | No | 4.9 (76) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174510/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174510.md) |
| Anglers Bay at One Particular Harbour 392-103 | Bradenton, FL | 3 | 7 | Yes | 5 (6) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-271103/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-271103.md) |
| Anna Cabana Bungalow #1 | Holmes Beach, FL | 1 | 2 | No | 4.9 (38) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174455/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174455.md) |
| Anna Cabana Bungalow #2 | Holmes Beach, FL | 1 | 2 | No | 4.9 (37) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174456/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174456.md) |
| Anna Cabana Bungalow #3 | Holmes Beach, FL | 1 | 2 | No | 4.8 (38) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174457/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174457.md) |
| Anna Cabana Bungalow #4 | Holmes Beach, FL | 2 | 4 | No | 4.9 (47) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174458/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174458.md) |
| Anna Maria Beach Place, Unit 3 | Holmes Beach, FL | 1 | 4 | No | 4.9 (9) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174514/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174514.md) |
| Anna Maria Beach Place, Unit 5 | Holmes Beach, FL | 1 | 4 | No | 4.9 (37) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174516/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174516.md) |
| Anna Maria Beach Place, Unit 6 | Holmes Beach, FL | 1 | 4 | No | 4.8 (34) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174517/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174517.md) |
| Bay Watch 6a | Bradenton Beach, FL | 2 | 4 | No | 4.3 (15) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174522/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174522.md) |
| Bayview Condo B | Bradenton Beach, FL | 2 | 6 | No | 4.6 (8) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-256701/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-256701.md) |
| Bayview Inn #101 | Bradenton Beach, FL | 1 | 4 | No | 4.9 (21) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-234316/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-234316.md) |
| Beachside | Holmes Beach, FL | 3 | 6 | No | 4.9 (36) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174536/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174536.md) |
| Beachview #5 | Holmes Beach, FL | 2 | 4 | No | 5 (3) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-274431/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-274431.md) |
| Bradenton Beach Club D | Bradenton Beach, FL | 3 | 8 | No | 4.7 (45) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174540/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174540.md) |
| Breakers 4 At Sandcastle #1 | Bradenton Beach, FL | 3 | 8 | No | 4.7 (53) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174543/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174543.md) |
| Bridgeport Condo 101 | Bradenton Beach, FL | 2 | 4 | No | 4.5 (15) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174545/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174545.md) |
| Bridgeport Condo 204 | Bradenton Beach, FL | 2 | 6 | No | 4.5 (17) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174445/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174445.md) |
| Bridgeport Condo 209 | Bradenton Beach, FL | 2 | 4 | No | 5 (12) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174446/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174446.md) |
| Bridgeport Condo 211 | Bradenton Beach, FL | 2 | 4 | No | 4.4 (7) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174546/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174546.md) |
| Coastal Cottage | Holmes Beach, FL | 3 | 6 | No | 5 (2) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-284000/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-284000.md) |
| Coco Cabana | Holmes Beach, FL | 3 | 6 | No | 4.9 (37) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174549/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174549.md) |
| Coquina Beach Club 101 | Bradenton Beach, FL | 2 | 4 | No | 4.7 (42) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174550/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174550.md) |
| Coquina Beach Club 102 | Bradenton Beach, FL | 2 | 6 | No | 4.9 (17) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-260960/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-260960.md) |
| Coquina Moorings 102 | Bradenton Beach, FL | 3 | 6 | No | 4.2 (17) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174552/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174552.md) |
| Coquina Moorings 202 | Bradenton Beach, FL | 2 | 6 | No | 4.6 (20) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174554/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174554.md) |
| Coquina Moorings 203 | Bradenton Beach, FL | 3 | 6 | No | 5 (15) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-260136/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-260136.md) |
| Coquina Moorings 204 | Bradenton Beach, FL | 3 | 6 | No | — | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-286390/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-286390.md) |
| Coquina Moorings 206 | Bradenton Beach, FL | 2 | 4 | No | 4.5 (24) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174555/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174555.md) |
| Cove at Sandy Pointe 112 | Holmes Beach, FL | 2 | 6 | No | — | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-274179/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-274179.md) |
| Cove At Sandy Pointe 208 | Holmes Beach, FL | 2 | 6 | No | 4.7 (22) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174560/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174560.md) |
| Escape to Serenity 2 Units | Holmes Beach, FL | 4 | 8 | Yes | 5 (1) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-254395/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-254395.md) |
| Escape to Serenity A | Holmes Beach, FL | 2 | 6 | No | 5 (7) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-254393/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-254393.md) |
| Escape to Serenity B | Holmes Beach, FL | 2 | 6 | Yes | 4.8 (6) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-254394/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-254394.md) |
| Fountainhead Condo 3 | Holmes Beach, FL | 2 | 6 | No | 4.6 (23) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174564/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174564.md) |
| Fountainhead Condo 4 | Holmes Beach, FL | 2 | 4 | No | 4.3 (18) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174565/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174565.md) |
| Gulf Sands 201 | Holmes Beach, FL | 2 | 6 | No | 5 (45) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174570/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174570.md) |
| Island Walk, Cove At Sandy Point 207 | Holmes Beach, FL | 2 | 6 | No | 4.8 (11) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-240263/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-240263.md) |
| La Playita 7 | Holmes Beach, FL | 2 | 6 | No | 4.9 (28) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-213680/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-213680.md) |
| Lakeside Beach House | Holmes Beach, FL | 3 | 6 | No | 4.8 (41) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174578/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174578.md) |
| LaPlage #3 | Holmes Beach, FL | 4 | 6 | No | 5 (7) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-265790/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-265790.md) |
| Lazy Livin 6 | Bradenton Beach, FL | 2 | 6 | No | 4.7 (26) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-216483/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-216483.md) |
| MI Happy Place Sand Castle 1 | Holmes Beach, FL | 2 | 6 | Yes | 4.9 (31) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174436/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174436.md) |
| MI Happy Place Sand Dollar 2 | Holmes Beach, FL | 2 | 6 | Yes | 4.8 (35) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174437/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174437.md) |
| MI Happy Place Sea Horse 3 | Holmes Beach, FL | 2 | 6 | Yes | 4.8 (27) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174487/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174487.md) |
| MI Happy Place Sea Turtle 4 | Holmes Beach, FL | 2 | 6 | Yes | 4.8 (24) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174488/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174488.md) |
| MI Happy Place-4 Units | Holmes Beach, FL | 8 | 16 | Yes | 4.9 (29) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174489/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174489.md) |
| Ocean Park Terrace 202 | Bradenton Beach, FL | 2 | 5 | No | 4.7 (3) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174581/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174581.md) |
| One Particular Harbour  Sound View 379-401 | Bradenton, FL | 2 | 5 | Yes | 4.9 (35) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-216784/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-216784.md) |
| One Particular Harbour 379-101 | Bradenton, FL | 2 | 5 | Yes | 4.9 (24) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-230259/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-230259.md) |
| One Particular Harbour 387-101 | Bradenton, FL | 2 | 5 | No | 4.9 (14) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-206954/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-206954.md) |
| One Particular Harbour 391-201 | Bradenton, FL | 2 | 5 | Yes | 4.8 (14) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-206004/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-206004.md) |
| One Particular Harbour 391-203 | Bradenton, FL | 3 | 6 | Yes | — | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-283886/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-283886.md) |
| One Particular Harbour 392-201 | Bradenton, FL | 2 | 5 | Yes | 4.9 (32) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-208713/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-208713.md) |
| One Particular Harbour 395-402 | Bradenton, FL | 3 | 7 | No | 5 (2) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-265896/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-265896.md) |
| One Particular Harbour 396-303 | Bradenton, FL | 3 | 6 | No | 5 (4) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-259917/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-259917.md) |
| One Particular Harbour Lagoon View 383-202 | Bradenton, FL | 3 | 7 | Yes | 4.8 (13) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-247410/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-247410.md) |
| One Particular Harbour Lagoon View 395-103 | Bradenton, FL | 3 | 7 | Yes | 4.9 (52) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-198297/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-198297.md) |
| Otter Lagoon at One Particular Harbour  379-103 | Bradenton, FL | 3 | 7 | Yes | 4.8 (12) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-256990/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-256990.md) |
| Palm Cay 3 | Holmes Beach, FL | 2 | 6 | No | 4.8 (23) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174584/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174584.md) |
| Palm Cay 4 | Holmes Beach, FL | 1 | 2 | No | 5 (8) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174585/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174585.md) |
| Palm Cay 5 | Holmes Beach, FL | 3 | 6 | No | 4.8 (23) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174586/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174586.md) |
| Palma Sola | Bradenton, FL | 3 | 8 | Yes | 5 (8) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-231137/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-231137.md) |
| Peace 'n Paradise | Holmes Beach, FL | 2 | 6 | No | 5 (44) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174490/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174490.md) |
| Pelican Cove 15 | Bradenton Beach, FL | 2 | 4 | Yes | 4.8 (29) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174588/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174588.md) |
| Pelican Place at The Nautilus | Holmes Beach, FL | 2 | 4 | No | 5 (12) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-261257/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-261257.md) |
| Penthouse View at One Particular Harbour 388-401 | Bradenton, FL | 2 | 5 | No | 5 (2) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-277058/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-277058.md) |
| Pool Party 2 Units | Holmes Beach, FL | 5 | 10 | Yes | 4.6 (5) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-237311/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-237311.md) |
| Pool Party North | Holmes Beach, FL | 2 | 4 | Yes | 4.7 (3) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-237312/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-237312.md) |
| Pool Party South | Holmes Beach, FL | 3 | 6 | Yes | 4.6 (9) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-237313/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-237313.md) |
| Sail Away Cottage | Bradenton Beach, FL | 3 | 6 | No | 4.7 (41) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174593/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174593.md) |
| Sand & Sun A SIDE | Holmes Beach, FL | 2 | 5 | No | 5 (1) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-275312/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-275312.md) |
| Sand & Sun B SIDE | Holmes Beach, FL | 1 | 4 | No | — | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-275313/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-275313.md) |
| Sandcastle 3 | Bradenton Beach, FL | 3 | 8 | No | 4.9 (47) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174595/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174595.md) |
| Sandy Pointe 210 | Holmes Beach, FL | 2 | 6 | No | 4 (8) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174596/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174596.md) |
| Sapphire Serenity | Holmes Beach, FL | 3 | 6 | No | 5 (3) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-278824/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-278824.md) |
| Sea Pirate 3 | Holmes Beach, FL | 2 | 6 | No | 4.9 (44) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174597/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174597.md) |
| Sea Pirate 7 | Holmes Beach, FL | 2 | 4 | No | 4.5 (20) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174599/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174599.md) |
| Sea-Esta | Holmes Beach, FL | 3 | 6 | Yes | 4.8 (26) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174600/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174600.md) |
| Seabreeze Condo B | Holmes Beach, FL | 2 | 6 | Yes | 4.8 (28) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174601/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174601.md) |
| Seaside Beach House 101 | Holmes Beach, FL | 2 | 4 | No | 4.7 (23) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174611/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174611.md) |
| Seaside Beach House 102 | Holmes Beach, FL | 1 | 4 | No | 4.5 (36) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174612/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174612.md) |
| Seaside Beach House 105 | Holmes Beach, FL | 2 | 4 | No | 5 (34) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174613/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174613.md) |
| Seaside Beach House 201 | Holmes Beach, FL | 2 | 4 | No | 4.8 (37) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174614/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174614.md) |
| Seaside Beach House 203 | Holmes Beach, FL | 1 | 3 | No | 4.8 (38) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-204602/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-204602.md) |
| Seaside Beach House 205 | Holmes Beach, FL | 2 | 4 | No | 4.8 (40) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174615/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174615.md) |
| Sirena Del Mar | Holmes Beach, FL | 3 | 6 | Yes | 4.8 (16) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174619/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174619.md) |
| So Beachy Chic | Holmes Beach, FL | 2 | 6 | No | — | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-261258/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-261258.md) |
| Southern Comfort | Holmes Beach, FL | 4 | 8 | Yes | 4.4 (15) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-178725/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-178725.md) |
| SS Salamander 2 Units | Holmes Beach, FL | 4 | 8 | No | 4.7 (15) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174492/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174492.md) |
| SS Salamander North | Holmes Beach, FL | 2 | 5 | No | 4.9 (20) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174493/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174493.md) |
| SS Salamander South | Holmes Beach, FL | 2 | 5 | No | 4.8 (16) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174494/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174494.md) |
| Sunset FantaSea at One Particular Harbour 380-202 | Bradenton, FL | 3 | 7 | No | 4.9 (8) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-262804/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-262804.md) |
| Sunset Terrace 108 | Bradenton Beach, FL | 2 | 6 | No | 4.8 (44) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174621/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174621.md) |
| Sunset Terrace 201 | Bradenton Beach, FL | 1 | 6 | No | 4.9 (47) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174623/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174623.md) |
| Sunset Villas | Holmes Beach, FL | 2 | 6 | No | 4.6 (10) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174448/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174448.md) |
| SWEPT AWAY B | Holmes Beach, FL | 2 | 6 | No | 5 (9) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-257566/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-257566.md) |
| Swizzle On The Sound | Holmes Beach, FL | 3 | 6 | Yes | 5 (12) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-218299/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-218299.md) |
| Terrace Condo 6 | Holmes Beach, FL | 2 | 6 | No | 4.9 (17) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-248621/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-248621.md) |
| The Palms #3 | Holmes Beach, FL | 2 | 4 | Yes | 5 (21) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-235198/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-235198.md) |
| The Palms #4 | Holmes Beach, FL | 2 | 6 | Yes | 5 (37) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-231331/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-231331.md) |
| The Sunset Retreat at One Particular Harbour 384-202 | Bradenton, FL | 3 | 7 | No | 4.9 (34) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-204768/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-204768.md) |
| Tortuga Cottage | Bradenton Beach, FL | 2 | 6 | Yes | 4.8 (11) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-277062/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-277062.md) |
| Turquoise Turtle at One Particular Harbour 388-403 | Bradenton, FL | 3 | 6 | No | 5 (5) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-248571/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-248571.md) |
| Waters Edge 102 N | Holmes Beach, FL | 2 | 4 | No | 4.9 (23) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174632/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174632.md) |
| Waters Edge 106s | Holmes Beach, FL | 1 | 4 | No | 4.8 (16) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174633/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174633.md) |
| Waters Edge 110s | Holmes Beach, FL | 2 | 5 | No | 4.6 (11) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174634/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174634.md) |
| West Bay Cove 131 | Holmes Beach, FL | 2 | 4 | No | — | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174503/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174503.md) |
| West Bay Cove 142 | Holmes Beach, FL | 2 | 5 | No | 4.9 (7) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174640/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174640.md) |
| West Bay Cove 213 | Holmes Beach, FL | 2 | 4 | No | — | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-278919/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-278919.md) |
| West Bay Cove 216 | Holmes Beach, FL | 2 | 4 | No | 5 (2) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174643/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174643.md) |
| West Bay Cove 223 | Holmes Beach, FL | 2 | 4 | No | 4.7 (6) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-207705/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-207705.md) |
| West Bay Cove 226 | Holmes Beach, FL | 1 | 6 | No | 4.4 (5) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174644/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174644.md) |
| West Bay Cove 231 | Holmes Beach, FL | 2 | 4 | No | 4.7 (3) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174508/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174508.md) |
| West Bay Cove 236 | Holmes Beach, FL | 2 | 4 | No | 4.9 (10) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174505/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174505.md) |
| West Bay Cove 238 | Holmes Beach, FL | 2 | 4 | No | 4.8 (6) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174506/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174506.md) |
| West Bay Cove 242 | Holmes Beach, FL | 2 | 4 | No | 5 (1) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-276790/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-276790.md) |
| WHILE AWAY 2 Units | Holmes Beach, FL | 4 | 8 | No | 5 (1) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-257568/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-257568.md) |
| WHILE AWAY A | Holmes Beach, FL | 2 | 6 | No | 4.7 (36) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174645/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174645.md) |
## Live availability for your dates
For live availability and pricing across this collection on specific dates, open this filtered search and fill in the dates:
https://www.islandvacationproperties.com/vacation-rentals/results/?searchform=1&cwrsearch=1&checkboxes=Pool&arrive_date=M/D/YYYY&depart_date=M/D/YYYY
(arrive_date = check-in, depart_date = checkout; dates as month/day/year, e.g. 12/15/2026)
This runs the live search on the website; hand it to the guest for bookable, up-to-the-minute results across the whole collection.