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Southwest Vacation Rentals

(3344 rentals)
Naples Condo
Sleeps 6, 3 bedrooms, 2 bathrooms
5 reviews

Distance to beach: 0.5 miles to Wiggins Pass

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

As soon as you arrive at Princeton Place in the Vanderbilt neighborhood of North Naples, you know you are at home. Beautiful, lush landscaping, lawns, pool, pond, and boat docks adorn this property. In addition, you will have access to the optional membership at the Tarpon Cove Yacht and Racquet Club....

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Featured review

"Just perfect"

Location was excellent and the condo was great. Everything was as advertised and then some. Chip, the owner, was very nice and responded very quickly to all questions and requests we had. Quiet area with...

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$186
avg per night
Punta Gorda Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

Are you looking for a winter getaway with plenty to do or nothing to do at all? Here is your spot! Enjoy a Comfortable, Brand New, Very Clean, Well-Stocked, Luxury condo in SWFL's favorite resort community. Step into your very own slice of paradise at Heritage Landing Golf and Country Club. This...

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$168
avg per night
Sarasota Condo
Sleeps 5, 3 bedrooms, 2 bathrooms
2 reviews

Distance to beach: 7 miles to Siesta Key Beach

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

****NEXT AVAILABLE LEASE DATE: July 15,2026 ($2,200 per mo. reflects July 1-Dec. 31 2026 dates)****($3,975 Jan., April & May 2027) *2 MONTH MINIMUM & 6 Month Max, No Pets & No Trucks***Serene, Spacious, & Clean, centrally located in Sarasota & in the beautiful Village Brooke, 1st...

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Featured review

"Village Brooke is a great location"

Village Brooke's location gives easy access to all of the Sarasota area and is a very peaceful and well maintained development. The owners of this unit were super helpful in providing the extra items we...

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$81
avg per night
Ave Maria Condo
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

NEW ON THE MARKET - AVAILABLE FOR MARCH 2026!! Spend your vacation in warm and sunny, Southwest Florida in this spectacular golf course/pool home. You'll enjoy tremendous sunsets from the beautiful pool, in this gated resort community, with golf course and water views. This home is available for...

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$367
avg per night
Fort Myers House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Nestled in a quiet enclave of newly constructed homes and attached villas you will find the gated community of Venetian Pointe. Just minutes from SW Florida's award winning beaches, shopping, dining, golf and professional baseball - you'll be secluded from the hustle and bustle, but close enough...

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$165
avg per night

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Marco Island House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Beautiful 3 Bedroom, 2 Bath plus Den waterfront home close to Mackle Park, Museum, YMCA, and the Island Racquet Center. Beautiful Pool area with lots of furniture for fun in the sun. Large living room and a separate family room. Office area for your working vacation and large kitchen to prepare meals....

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$357
avg per night
Fort Myers House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Tucked away beneath towering palms and surrounded by lush tropical greenery, this hidden South Fort Myers retreat feels worlds away from the crowds — yet beaches, restaurants, shopping, and entertainment are all just minutes from your doorstep. If you’ve been searching for a vacation home...

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$192
avg per night
Bonita Springs Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

Stunning high-rise condo on Hickory Island, boasting views of the Gulf of America and the surrounding back bay. Sit back and enjoy unobstructed views of sunsets and sunrises and watch the dolphins, manatees and boaters go by! With the added bonus of a boat dock where you can tie up your boat rental,...

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$223
avg per night
Estero House
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 9 miles to Ft Myers Beach

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Located in Stoneybrook Estero a gated secured community. Spacious 3 bed, 2 bath open concept home sleeps six. Private pool with spa under a fully covered screened lanai overlooking the golf course with beautiful sunset views. Community offers tennis courts, pickleball, volleyball, basketball, bocce,...

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$291
avg per night
New
Bonita Springs House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

We’re excited to welcome you to our newly renovated waterfront retreat off the Imperial River, where luxury, comfort, and true Southwest Florida living come together. From the moment you arrive, you will feel relaxed, at home, and ready to enjoy the sunsets, water views, and peaceful moments that...

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$400
avg per night
New
Punta Gorda House
Sleeps 10, 5 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

Seasonal Rental in Gated Punta Gorda Community – Perfect for Families, Couples & Future SWFL Home BuyersEscape to Southwest Florida in this spacious two-story home located in a beautiful gated community in Punta Gorda. Thoughtfully designed with a first-floor primary suite, this home is...

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$103
avg per night
Marco Island House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Our CLEAN, no -smoking 3 bedroom, 2 bath fully furnished house with a heated pool is ideally located !! Walk to the beach via the Public Beach Access by the Marriott Crystal Shores, only a quick one block away.“The Marco Walk Plaza” is also one block away, with its many restaurants, "dinner...

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$350
avg per night
Alva Villa
Sleeps 5, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Newer, furnished with high end furnishings. This beautiful one level 2 bedroom+den, 2 bathroom villa is peaceful, water views. 30 day lease minimum. 4 month minimum for winter months. No pets.Looking for a 4 month lease during winter season.Golf Membership is transferable with a fee.$2,000...

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Featured review

"Riverhall"

Location was excellent Walking distance to club house and bunker bar. Landlord very responsive and very easy to deal with. Would recommended his unit.

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$139
avg per night
Bonita Springs Condo
Sleeps 6, 3 bedrooms, 2 bathrooms
3 reviews

Distance to beach: 12 miles to Barefoot beach Bonita Springs

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner

About this property

Welcome to your Florida retreat!This beautifully furnished 3-bedroom, 2-bathroom condo (1,299 sq. ft.) is located in the sought-after Bonita National Golf & Country Club, where resort amenities and a vibrant social scene create the perfect setting for an active resort lifestyle.Interior &...

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Featured review

"Lovely 3 bedroom condo"

This delightful 3 bedroom condo is just a short walk to both a satellite pool and a gorgeous resort style pool , complete with hot tub and a cascading waterfall. You can enjoy drinks and lunch at the poolside...

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$137
avg per night
Sarasota Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
8 reviews

Distance to beach: 3 miles to Siesta Key

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

My wife and I are recently retired educators. We ARE NOT multiple rental property owners. We own this one condo and are snowbirds from Pennsylvania. Our place is newly remodeled floor to ceiling! The Oasis complex is a prime location in close proximity to downtown Sarasota, Siesta Village, & nationally...

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Featured review

"Beautiful condo in a great location!"

I really enjoyed my stay at Gary and Terri's beautiful condo. The kitchen and bathrooms have been updated and are beautiful. The screened in porch and private patio were a plus and a great place for morning...

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$90
avg per night
Ave Maria Condo
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

Super desirable Arrowhead Coach home, fully furnished and offering 3 bedrooms, 2 bathrooms, and a 2-car garage. This beautiful ranch-style model (no stairs!) features over 1,700 square feet of living space, including a large screened lanai with stunning lake and golf course views—perfect for relaxing...

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$210
avg per night
New
Punta Gorda Condo
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

3 Bedrooms - Master: King size bed, on-suite bathroom (standing shower and 2 sinks), 2 walk in closest, dresser, TV with a ceiling fan - Guest room #1: TV, King bed, walk in closet, dresser, access to the 2nd bathroom 1 sink, and bathtub/shower combo, and ceiling fab - Guest room #2: TV, queen size...

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Featured review

"Home Away From Home"

If "Paradise Found" was a physical address, this would definitely be it. From the moment we unpacked our bags, the rest of the world completely ceased to exist. Clean, spacious, beautifully equipped, and...

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$167
avg per night
Cape Coral Villa
Sleeps 6, 4 bedrooms, 3 bathrooms
3 reviews

Distance to beach: 7 miles to Yacht Club Cape Coral

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Wow- What a dream villa! - This is the reaction of most tenants when you enter the Villa Beach Tower.This villa is very special. Plenty of space for up to six people, divided in high-quality individually furnished bedrooms and three luxurious bathrooms, as well as a living room in Florida-style with...

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Featured review

"Villa Beach Tower"

A beautiful home, extremely well appointed and supplied. The pool area is fantastic with a convenient outdoor kitchen/grill. Most of our time was spent outdoors in the gorgeous salt water pool…perfect...

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$276
avg per night
New
Punta Gorda House
Sleeps 11, 3 bedrooms, 2.5 bathrooms

Distance to beach: 27 miles to Englewood

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Our 3-bedroom, 2 1/2-bathroom private pool+hot tub vacation home is the best option for a quiet and beautiful waterside stay. A mile from the incredible shopping and dining found at Fishermans Village & historic Punta Gorda Downtown.Punta Gorda Private Pool+Spa Home Sleeps 11+ 3 Bedrooms / 2...

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$367
avg per night
Siesta Key Apartment
Sleeps 4, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Come stay and relax on Siesta Key! Home of the #1 Beach in USA. Award-winning white sand beaches await. Beautiful first floor, 1 bedroom w/den in Bayside community of Bay Oaks. 3 TV's. Sleeps 4 (King in master bedroom, den has a twin bed and living room has a sleeper sofa. Complex offers swimming...

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$134
avg per night
Fort Myers Beach House
Sleeps 8, 3 bedrooms, 4 bathrooms
2 reviews

Distance to beach: 180 yards to Fort Myers Beach

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

It's Island Time! Welcome to your family’s ultimate getaway—a 3 bedroom, 3+ bath large beach home in a neighborhood with its very own beach access and bayside park with a delightful tiki. But that’s just the beginning of the adventure that awaits!Step inside and discover a haven...

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Featured review

"Wonderful time!"

A wonderful time for our group!! House worked out nicely. Pool was great. The close location to the beach was awesome. Susan was so helpful. Such a good experience. Thank you so much Susan!!

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$458
avg per night
Sarasota Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

One of the BEST locations in the community! Very close to all amenities on site to ensure you have a wonderful vacation. Spotlessly clean well appointed 2 bed 2 bath villa includes Free WIFI, cable and smart TVs as well as dishwasher, washer and dryer. Conveniently located - the famous Siesta Key...

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Featured review

"Debby Downer"

Tropical Storm Debby tried to rain on our parade. After dumping much rain and a downed tree. Myself and a couple others cleared the tree so we could exit the premises. The weather turned gorgeous and...

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$199
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
3 reviews

Distance to beach: 200 yards to Siesta Key Crescent Beach

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

SIESTA SUMMER SAVINGS! RECEIVE 10% OFF YOUR SUMMER STAY BETWEEN 5/30/26 AND 8/29/26 WHEN BOOKING DIRECTLY ONLINE AT THE ANCHORAGE YACHT & TENNIS CLUB IN-HOUSE RENTAL PROGRAM WEBSITEWe invite you to stay in our spacious 2 bed 2 bath condo, 'Siesta Chillin', across from the beautiful crystal...

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Featured review

"Siesta Central - The Anchorage!!"

We stayed at the Anchorage in unit 305. It faces the city and the inner coastal lagoon. We were treated to a dolphin show one evening when they entered the lagoon searching for food!! This location...

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$221
avg per night
Naples Condo
Sleeps 2, 1 bedroom, 1 bathroom
1 review

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner

About this property

Super cute 2nd floor condo 5 minute walk from 5th Avenue. Great position within this small complex with pool and tropical views from both the the lanai and preferred front facing bedroom. New King bed and mattress for your comfort! New floor tile throughout. Enjoy the playful mocking birds putting on...

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Featured review

"Great spot which I’d stayed there!"

Naples is such a wonderful town, with so much to do. This condo was in a perfect location by what we read, and close to enjoy many of the wonderful areas in Naples. The beaches, close restaurants and fun...

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$95
avg per night
Ave Maria House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Gorgeous Brand New furniture now negotiable! Discover the sought-after Egret floorplan in the exclusive gated community of Del Webb Naples! This elegant 2 bedroom + den, 2 bathroom home offers a thoughtfully designed layout with luxurious features sure to impress. The chef’s kitchen is a standout...

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$167
avg per night
Fort Myers Apartment
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

Distance to beach: 3 miles to multiple

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Pool
  • Rentals by owner
  • WiFi

About this property

Welcome to our newly renovated condo in the beautiful community of Kelly Greens. Every detail of this spacious 2-bedroom, 2 baths unit was designed to have your comfort in mind. About the unit: LIVING ROOM:  65” HDTV for family time  Cozy fireplace  Comfortable sofa with pillows...

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Featured review

"Clean, Modern and Comfortable!"

We rented this newly updated condo in Kelly Greens. Everything was new and it felt like home! If there was something I needed, it was ordered for me.I would suggest that the unit have beach chairs...

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$148
avg per night
Englewood House
Sleeps 8, 3 bedrooms, 2 bathrooms

Distance to beach: 3 miles to Englewood Beach

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Attention Snowbirds. Three bedroom Two bath private home available with open floor plan. Perfect for family gatherings. Large master bedroom and bath are separated from the two guest bedrooms. Outside is a large swimming pool with large deck and covered porch when you need to escape the sun. Located...

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$200
avg per night
New
Anna Maria Island House
Sleeps 8, 4 bedrooms, 3.5 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to Salt and Shore by Coastal Chic Vacations!- Steps to Anna Maria Island's white sandy beaches - Community heated pool - Private putting green - 4 spacious bedrooms & 4 bathrooms - Ground level home - Close proximity to local dining, grocery store, shops... - Beach gear provided -...

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$289
avg per night
Marco Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pool
  • WiFi

About this property

NOTE: This building will have construction being done on the 01 and 02 balconies starting August 5 and last thru October 2026. Noise maybe heard throughout the building! POOL will be closed August 3 till at least September 25! Beach access will be available! Lobby is currently under construction and unavailable....

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$271
avg per night
Venice Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
5 reviews

Distance to beach: 5 miles to Venice Beach

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Beautiful lake view large ground floor condo with 2 large bed rooms each is ensuite with its own bath.and covered carport. Both front and rear heated / air-conditioned glassed in secure lanai's appointed with ceiling fans with light kits, with 1 new king sized remote controlled bed for late night...

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Featured review

"Another wonderful stay in Venice"

This place is really perfect. Tom and Kay are fantastic owners and their condo is ideal. The pool couldn’t be more convenient and all the beaches around Venice are beautiful. A little farther away to...

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$97
avg per night
Estero Condo
Sleeps 2, 1 bedroom, 1.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

Experience Estero like a local in this lovely 1-bedroom condo. Walk to dozens of shops and restaurants in minutes. Enjoy the pool, jacuzzi and community gym. Watch the sunrise above a beautiful lake in the morning. 10 min drive to beautiful Bonita Beach. The space features a comfortable king bed and two...

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$160
avg per night
Cape Coral Villa
Sleeps 8, 4 bedrooms, 3 bathrooms

Distance to beach: 6 miles to Yacht Club Cape Coral

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Villa Tuscany - Villa with south facing locationVilla Tuscany is situated on a large plot in a quiet area but yet close to many restaurants and shopping.Staying at the large pool area puts you every day new in a holiday mood. Plenty of sunshine with south exposure of this beautiful villa plus...

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$225
avg per night
Venice Mobile home
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

Distance to beach: 2 miles to Venice Beach and others

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Pool
  • Rentals by owner
  • WiFi

About this property

Just what you need!! --2 Bedrooms, 2 baths well-kept and modern --Tastefully furnished and decorated --Pleasant lanai to enjoy Florida breezes --All utilities included --Air conditioning --Wireless Internet provided --Beautifully maintained lot --Washer and dryer onsite --Pets upon approval...

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Featured review

"2 months in paradise"

We stayed in this unit this past Feb and March. This place was lovely and clean. We enjoyed Bay Indies and all it offers. The host was on site and available. We would definitely recommend it.

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$61
avg per night
Sarasota House
Sleeps 7, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Bright and cozy 3BR/2BA Sarasota getaway, just 15 minutes from Siesta Key and Lido Key beaches.Arlington Park & Pool is right across the street, and the popular Hillview shops and restaurants are just minutes away.Downtown is a 6 minute drive away, and some of Sarasota's biggest attractions...

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$304
avg per night
Marco Island Condo
Sleeps 5, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pool
  • WiFi

About this property

This updated beachfront condo features two new full bathrooms with walk-in showers, a modern kitchen with new appliances, fresh flooring, and brand-new beds and furniture. Enjoy the convenience of ceiling fans and three new smart TVs.The condo offers an outstanding view from its two bedrooms and...

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$282
avg per night
Bonita Springs Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Bright and spacious (1700 sq. ft.) 2nd floor condominium, located in the gated Spanish Wells community in an idyllic, quiet cul-de-sac with lake view. Featuring: 2 bedrooms (master and guest), den and 2 bathrooms. Comfortably furnished and boasting a large living and dining area and large open plan kitchen...

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$194
avg per night
Fort Myers Beach Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

2 Bedroom (1 King, 2 twins)/2 Bath (1 shower, 1 tub/shower) Fort Myers Beach condo sits just across the road from the wide, quiet beaches at the southern end of the island. You will enjoy this private end-unit view overlooking permanently preserved land and no through-traffic. Enter through the screened...

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$172
avg per night
Naples House
Sleeps 6, 3 bedrooms, 2 bathrooms
4 reviews

Distance to beach: 5 miles to Lowdermilk Park

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Christmas 2026 is available, because of cancellation!The modern furnished villa with 2.000 ft² has 3 bedrooms and 2 bathrooms. Each bedroom has a flat-screen TV. In the spacious living and dining area you can find a place to relax on the couch. The large LED TV in the living room is connected...

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Featured review

"Amazing property, had everything tha we needed."

This property is everything it says and more. Everything we needed besides food was provided and even had basics of things there to use. Very clean and very fancy. Gated community is beautiful and felt...

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$242
avg per night
Fort Myers Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
5 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

This property is located in Southwest Florida close to many attractions and services. Located less than 4 miles to the beautiful stunning white sand beaches. Condominium offers 1500 square feet, 2 bedroom, 2 bath home. Large Master Bedroom includes King Sized bed with walk in closet and fully furnished...

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Featured review

"Quiet Retreat"

What a wonderful property with swift access to so much! Pop down to Naples, or over to Sanibel or just stay in town for great restaurants and quiet beach access. Wonderful, generous, hosts who went above...

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$87
avg per night
Bradenton Condo
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

Welcome to One Particular Penthouse at One Particular Harbour Margaritaville! Elevated Penthouse Living with Stunning Views from Your Private Lanai Short drive to the World-Class Beaches of Anna Maria Island Community Pool, Splash Pad, Playground & Activity Area Walk to Floridays or enjoy...

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$306
avg per night
Cape Coral House
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

The area beaches are open for your enjoyment!Get ready to relax and refresh in this Southwest Cape Coral heated pool home. Whether on the water, or in the pool, your time will be spent soaking in the sun rejuvenating your yourself, your family, and your friends.At this property you will enjoy: A...

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$185
avg per night
Siesta Key Bungalow
Sleeps 6, 2 bedrooms, 2 bathrooms
4 reviews

Distance to beach: 0.5 miles to Siesta Beach access 7

Key Amenities

  • Air conditioning
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

The Canal Place Bungalow Old Florida Charm on the Water in Siesta KeyEscape to the timeless beauty of Siesta Key with a stay at Canal Place, a spacious 2-bedroom, 2-bath bungalow full of vintage Florida character. Nestled along a peaceful canal with its own dock, this retreat blends classic charm...

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Featured review

"My stay at the Canal Place in Siesta Bungalows"

I am thoroughly enjoying my stay at Siesta Bungalows!!! My place is clean, quiet, and in a fabulous location!! I am about a 5 minute walk to the village and only a 7 min walk from the breathtaking Siesta...

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$155
avg per night
Port Charlotte House
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 10 miles to Boca Grande

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Book your Florida Spring BreakMay -July available.Picture yourself enjoying a gorgeous view down the intersecting canal.Imagine sitting by the heated pool and enjoying the private tranquil uninterrupted views sipping your favorite tropical beverage. Eagles , gators and other wildlife are common...

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$163
avg per night
Ave Maria Condo
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

This beautifully furnished Arrowhead model coach home in the heart of Ave Maria and enjoy a lifestyle that blends comfort with convenience. Thoughtfully designed with spacious open living areas, this home is move-in ready and styled to perfection. The Arrowhead floor plan offers generous bedrooms, a modern...

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$243
avg per night
Englewood Condo
Sleeps 5, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

January special!!! Just dropped by $500.00Welcome to Sun, Sand & Serenity! Walk in, kick off your shoes, and relax. This sun filled 2 bedroom/2bath plus loft with extra bed and with a lanai condo is ready to be your home away from home with a coastal feel and an open floorplan.Pelican Landing...

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$154
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 3 bathrooms
63 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Steps to Beach + Heated Pool + Putting Green + Golf Cart | WavesWelcome to Waves, your beautifully remodeled coastal retreat on Anna Maria Island — where modern luxury, effortless beach access, and resort-style outdoor living create the ultimate island escape.Perfectly positioned just across...

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$1,052
avg per night
Fort Myers Villa
Sleeps 6, 3 bedrooms, 3.5 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

Happiness is Rentable: The Lakehouse in South Fort MyersWelcome to The Lakehouse, a beautifully designed, spacious retreat nestled on a serene lake in the charming McGregor Woods community of South Fort Myers—Florida’s renowned “City of Palms.” This architect-designed 3,100...

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Featured review

"Outstanding vacation Rental"

We had a wonderful stay for two months at The Lake House in McGregor Woods—it truly lived up to its description and more. The home is beautifully designed, incredibly spacious, and perfectly set on a...

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$280
avg per night
Naples Condo
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Distance to beach: 3 miles to Bonita Beach

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

This condo is located in North Naples in the much sought out gated community of Sterling Oaks. CLOSE TO BEACHES. Unit consists of 3 bedrooms and 2 full baths, living room, dining area, large kitchen plus breakfast bar and an enclosed lanai. There’s covered parking at your door and additional parking...

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Featured review

"Two month stsy"

Susan was a great host. She met us at the condo and had little welcoming touches thoughout. The condo split layout worked great when our kids and grandkids visited. We enjoyed the community and amenities....

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$120
avg per night
Estero Condo
Sleeps 2, 1 bedroom, 1 bathroom
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Rental Rates for Winter 2027 December is $125 per night -January 5,000 for the month -February 5,000 for the month -March 5,000 for the month Book 2 months get 200 dollars off Price includes application fees and cleaning fees.Inside the Condo: • All new appliances in 2025 • Fully...

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Featured review

"Jake’s place was great"

Jake’s place was awesome clean. I loved it very clean. He was very nice host. The community was great. Had a golf course pool gym everything you need and conveniently located to sores in the airport.

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$171
avg per night
Siesta Key Villa
Sleeps 8, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

3 Bedroom/ 3 Bath Beachfront Townhome in Siesta Village, offering beautiful sunsets from your 2 balconies. Note that the beach directly in front of the property is private and may not allow access. Public beach access is always available just a few steps away. Go a block behind the unit to all the restaurants...

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$566
avg per night
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