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Avg / night: $269. Oceanside Home w/ Sunset Views of Sarasota Bay - Snowbirds Welcome, Dogs OK | Located in Sarasota, FL | 4.44 Stars | 3 Bed, 3 Bath | Pet-friendly. Dog-friendly. Max 6 guests. Discover your ideal Sarasota escape with this beautifully appointed bayfront vacation home, where fresh sea breezes, golden sunshine, and tranquil surroundings offer a relaxing retreat for up to six gues...
$2,206
5 Bedroom 6.5 baths Dog-friendly 4.2 30 reviews What our guests are saying... AI-generated...
Avg / night: $2,206. Beachfront estate near Sarasota with spectacular gulf views | Located in Nokomis, FL | 4.2 Stars | 5 Bed, 6.5 Bath | Pet-friendly. Dog-friendly. Max 12 guests. Villa De La Mar at Casey Key ~ Just South Of Sarasota And Steps From Stunning Nokomis Beach With Newly Reduced Nightly Rates! Casey Keys is fully up and running, showcasing its beauty and delivering unforgettable exp...
Avg / night: $203. Dog-friendly sunny stay with deck, grill, & W/D - internet & central AC | Located in Venice, FL | 1 Bed, 1 Bath | Pet-friendly. Dog-friendly. Max 4 guests. Nestled in a prime Venice location, this beautiful stay is located just minutes from numerous restaurants, movie theaters, shops, golf clubs, and of course, beaches! Full of sunlight and updated furnishings, inside Coastal...
Avg / night: $363. Renovated dog-friendly home near beach with private pool, screened lanai, grill | Located in Englewood, FL | 3 Bed, 2 Bath | Pet-friendly. Dog-friendly. Max 6 guests. Treat yourself and your family to a well-deserved escape at this peaceful, renovated home - perfect for both families and snowbirds. As you step inside, you ll see vinyl plank flooring and tile throughout the ho...
$325
4 Bedroom 3 baths Dog-friendly 2 reviews window.Vacasa = window.Vacasa || {}; $.extend(true,...
Avg / night: $325. Inviting dog-friendly home with yard, firepit, central AC, & W/D | Located in Sarasota, FL | 4.0 Stars | 4 Bed, 3 Bath | Pet-friendly. Dog-friendly. Max 8 guests. Newly renovated, stylish, cozy, and airy, you'll love this home near the Siesta Keys. Spend your days on the beach collecting shells, paddleboarding, fishing, or boating, and when you're done, tour the area for fun ...
Avg / night: $318. Single-story home with private yard, AC, & W/D - walk to beach, & dog-friendly | Located in Englewood, FL | 5.0 Stars | 2 Bed, 2 Bath | Pet-friendly. Dog-friendly. Max 4 guests. This gorgeous Gulf Coast getaway will have you living it up with family or friends just steps from the sugar-white shores of Englewood Beach. Set in the heart of Manasota Key, you'll have the best of ...
Avg / night: $572. Radiant home with heated pool, alfresco dining, W/D, and AC - dog-friendly | Located in Sarasota, FL | 4.87 Stars | 4 Bed, 3 Bath | Pet-friendly. Dog-friendly. Max 10 guests. The very best of the Sunshine State awaits you and your loved ones at this pleasant Sarasota home set just minutes away from Siesta Key! Nestled in a prime location for beach days, the sand and surf are ...
Avg / night: $286. Dreamy beach condo with AC & balcony - walk to nature park & near downtown | Located in Sarasota, FL | 4.86 Stars | 2 Bed, 2 Bath | Pet-friendly. Dog-friendly. Max 6 guests. Welcome to the Lido Del Mare! This beautiful condo was renovated in April 2025 and has everything you need to enjoy comfort, relaxation, and bliss while soaking in the sun. This stunning condo is in the p...
Avg / night: $259. Renovated dog-friendly home near beach with private pool, screened lanai, grill | Located in Englewood, FL | 3 Bed, 2 Bath | Pet-friendly. Dog-friendly. Max 6 guests. Treat yourself and your family to a well-deserved escape at this peaceful, renovated home - perfect for both families and snowbirds. As you step inside, you ll see vinyl plank flooring and tile throughout the ho...
Avg / night: $144. Dog-friendly sunny stay with deck, grill, & W/D - internet & central AC | Located in Venice, FL | 1 Bed, 1 Bath | Pet-friendly. Dog-friendly. Max 4 guests. Nestled in a prime Venice location, this beautiful stay is located just minutes from numerous restaurants, movie theaters, shops, golf clubs, and of course, beaches! Full of sunlight and updated furnishings, inside Coastal...
Avg / night: $227. Single-story home with private yard, AC, & W/D - walk to beach, & dog-friendly | Located in Englewood, FL | 5.0 Stars | 2 Bed, 2 Bath | Pet-friendly. Dog-friendly. Max 4 guests. This gorgeous Gulf Coast getaway will have you living it up with family or friends just steps from the sugar-white shores of Englewood Beach. Set in the heart of Manasota Key, you'll have the best of ...
Avg / night: $412. Radiant home with heated pool, alfresco dining, W/D, and AC - dog-friendly | Located in Sarasota, FL | 4.87 Stars | 4 Bed, 3 Bath | Pet-friendly. Dog-friendly. Max 10 guests. The very best of the Sunshine State awaits you and your loved ones at this pleasant Sarasota home set just minutes away from Siesta Key! Nestled in a prime location for beach days, the sand and surf are ...
Avg / night: $204. Dreamy beach condo with AC & balcony - walk to nature park & near downtown | Located in Sarasota, FL | 4.86 Stars | 2 Bed, 2 Bath | Pet-friendly. Dog-friendly. Max 6 guests. Welcome to the Lido Del Mare! This beautiful condo was renovated in April 2025 and has everything you need to enjoy comfort, relaxation, and bliss while soaking in the sun. This stunning condo is in the p...
Avg / night: $192. Oceanside Home w/ Sunset Views of Sarasota Bay - Snowbirds Welcome, Dogs OK | Located in Sarasota, FL | 4.44 Stars | 3 Bed, 3 Bath | Pet-friendly. Dog-friendly. Max 6 guests. Discover your ideal Sarasota escape with this beautifully appointed bayfront vacation home, where fresh sea breezes, golden sunshine, and tranquil surroundings offer a relaxing retreat for up to six gues...
$232
4 Bedroom 3 baths Dog-friendly 2 reviews window.Vacasa = window.Vacasa || {}; $.extend(true,...
Avg / night: $232. Inviting dog-friendly home with yard, firepit, central AC, & W/D | Located in Sarasota, FL | 4.0 Stars | 4 Bed, 3 Bath | Pet-friendly. Dog-friendly. Max 8 guests. Newly renovated, stylish, cozy, and airy, you'll love this home near the Siesta Keys. Spend your days on the beach collecting shells, paddleboarding, fishing, or boating, and when you're done, tour the area for fun ...
Partial Matches Found
Partial Matches Found
We found 69 more vacation rentals for Dog: Osprey Vacation Rentals that partially match or are similar
Avg / night: $213. Spacious home with enclosed pool and patio and near attractions | Located in Venice, FL | 4.0 Stars | 3 Bed, 2 Bath | Pet-friendly. Dog-friendly. Max 6 guests. Welcome to this fully remodeled and family-friendly vacation home in the heart of Venice, Florida. This charming South Venice pool home is situated on an oversized fenced-in corner lot on a quiet street, offering a pea...
850-378-4648
Avg / night: $777. Spacious duplex with private beach access & deck - dog-friendly | Located in Englewood, FL | 4 Bed, 3 Bath | Pet-friendly. Dog-friendly. Max 10 guests. **Snowbird friendly Unit with NEWLY ADVERTISED snowbird discounts for January, February, March and April! For stays 29-nights or more, additional discounts may be available, please contact Vacasa for more information. Our Exte...
Avg / night: $257. Breezy coastal duplex with private beach access & deck- dog-friendly | Located in Englewood, FL | 4.7 Stars | 2 Bed, 1 Bath | Pet-friendly. Dog-friendly. Max 4 guests. **Snowbird friendly Unit with NEWLY ADVERTISED snowbird discounts for January, February, March and April! For stays 29-nights or more, additional discounts may be available, please contact Vacasa for more infor...
Avg / night: $208. Coastal duplex with private beach access & deck - dog-friendly | Located in Englewood, FL | 3.9 Stars | 2 Bed, 1 Bath | Pet-friendly. Dog-friendly. Max 4 guests. **Snowbird friendly Unit with NEWLY ADVERTISED snowbird discounts for January, February, March and April! For stays 29-nights or more, additional discounts may be available, please contact Vacasa for more information...
Avg / night: $366. Dog-friendly house with pool, lanai, firepit, grill, patio, & enclosed backyard | Located in Sarasota, FL | 5.0 Stars | 4 Bed, 3 Bath | Pet-friendly. Dog-friendly. Max 9 guests. Centrally located close to Siesta Key Beach, this fantastic and well-equipped home is the perfect choice for your next escapade with family and friends! Find yourself just a short drive from restauran...
Avg / night: $212. Quiet home on a cul-de-sac with screened patio, bikes, W/D, & central AC | Located in Sarasota, FL | 4.4 Stars | 3 Bed, 2 Bath | Pet-friendly. Dog-friendly. Max 7 guests. Family-friendly comfort within easy reach of the beach and local entertainment is yours at this gorgeous Gulf Gate getaway. Boasting walking distance to the cultural hotbed of local shops and dining options ...
Avg / night: $153. Dog-friendly sunny stay with private pool, patio, full kitchen, sunroom & W/D | Located in Venice, FL | 4.5 Stars | 2 Bed, 2 Bath | Pet-friendly. Dog-friendly. Max 6 guests. Nestled in a prime Venice location, this beautiful home is located minutes away from the city's numerous restaurants, fishing charters, bicycle paths, movie theaters, shops, golf clubs, and of course, bea...
Avg / night: $300. Canalfront, Dog-Friendly Condo w/ High-Speed WiFi & Central AC - Snowbirds OK | Located in Bradenton Beach, FL | 4.29 Stars | 2 Bed, 2 Bath | Pet-friendly. Dog-friendly. Max 6 guests. All set on the ground floor, this light and bright condo provides an excellent family-friendly space to relax during your beach vacation. The waterfront location means you'll be close to the act...
Avg / night: $210. Dog-friendly duplex with outdoor living area - walk to beach/downtown | Located in Venice, FL | 5.0 Stars | 2 Bed, 1 Bath | Pet-friendly. Dog-friendly. Max 4 guests. Discover historic downtown charm, dig for sharks' teeth, or hit the on-site pool when you make this delightful duplex your home for an escape to the Suncoast. Steps from the heart of downtown, you'll be within ea...
Avg / night: $360. Single-story duplex near beach with renovated interior, AC-Dogs ok | Located in Osprey, FL | 2 Bed, 2 Bath | Pet-friendly. Dog-friendly. Max 6 guests. Iconic local attractions like Casey Key Beach, Oscar Shearer State Park, and Historic Spanish Point are all located within minutes of this beautifully renovated duplex. Retail shops, waterfront dining options, and family-friend...
Avg / night: $296. Updated, canal-front, dog-friendly condo with lanai & pool - walk to beach | Located in Siesta Key, FL | 4.67 Stars | 2 Bed, 2 Bath | Pet-friendly. Dog-friendly. Max 4 guests. Sitting directly on Turtle Bay Canal, this updated, first-floor condo puts you in a prime position to enjoy the spectacular sands of Siesta Key, an easy half-mile walk or bike ride away. If you d rather...
Avg / night: $213. Old Florida bungalow with WiFi, AC, washer/dryer, & patio - walk to beach | Located in Englewood, FL | 4.75 Stars | 2 Bed, 1 Bath | Pet-friendly. Dog-friendly. Max 6 guests. From the bay to the beach, this two-bedroom bungalow offers the best of Gulf Coast living. This family-friendly retreat boasts easy walking distance to the beach and great local dining options. Sarasota a...
Avg / night: $180. Renovated retreat - dog-friendly yard, AC & W/D - snowbirds welcome | Located in Sarasota, FL | 4.18 Stars | 2 Bed, 2 Bath | Pet-friendly. Dog-friendly. Max 6 guests. Located on a quiet cul-de-sac in Alta Vista, this renovated home features a pristine interior with a large yard, an open-concept floor plan, and new furnishings. Create your favorite dishes in the kitchen, equip...
Avg / night: $307. Renovated duplex near beach with central AC & private W/D-Dogs ok | Located in Osprey, FL | 2 Bed, 2 Bath | Pet-friendly. Dog-friendly. Max 6 guests. This renovated duplex offers updated comfort and a convenient location just minutes from local attractions like Casey Key Beach, Oscar Shearer State Park, and Historic Spanish Point. Retail shops, waterfront dining options, and ...
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