50 Best Sanibel Island Vacation rentals on Holiday Lettings - Cottages

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360 Vacation rentals

(8) Excellent 

24

Sanibel Island Vacation home rental

Southwest Gulf Coast / Sanibel Island

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
Surfsound home is tucked away off Rabbit Road and is just a 5 minute walk to deeded beach access. This beautiful spacious home offers 3 bedrooms (1 US king, 1 queen and one twin), 3 ½ bathrooms, fully equipped kitchen private screened heated pool and beautiful décor. Su …see more

from $150 / night

$1200 - $1500 / week

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from $150 / night

(1) Excellent 

17

Vacation condo in Sanibel Island

Southwest Gulf Coast / Sanibel Island

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
29 steps to the beach Just a few steps from our English owned luxury apartment and you are on the beach, a short walk from Sanibel's famous fishing pier. You will see small boats, pelicans and dolphins in the bay. Sanibel is famous for its beautiful white sandy shelli …see more

from $272 / night

$1900 - $2068 / week

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from $272 / night

24

Home rental in Sanibel Island with golf nearby

Southwest Gulf Coast / Sanibel Island

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Lea by the Sea is a luxurious 5 BEDROOM beach house with its own private beach and large panoramic windows overlooking San Carlos Bay . The house was completely remodeled in 2010. It has flat screen televisions in all bedrooms and a 48 inch tv in the great room. It ha …see more

from $856 / night

$5988 - $6999 / week

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from $856 / night

(3) Excellent 

24

Vacation condo rental

Southwest Gulf Coast / Sanibel Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
'' SEAS THE DAY '' condo is right on the beach , on the Gulf of Mexico , you just can't get away from the beach , you can't get closer . This beautiful 1300 SQ.FT. 3rd floor CORNER UNIT condo with 2 verandas wrapping around it, giving it a great sense of space and ope …see more

from $213 / night

$1489 - $3338 / week

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from $213 / night

24

Vacation villa with golf nearby in Sanibel Island

Southwest Gulf Coast / Sanibel Island

4 8 30 nights min

  • 4 bedrooms
  • Sleeps 8
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This recently redecorated south facing villa is situated in a quite but central part of Sanibel called Lake Murex . It is a spacious 4 bedroom, 3 full bath villa with a large open plan living area. The veranda overlooks the lake , the pool and the garden. There's a la …see more

from $356 / night

$2488 - $2789 / week

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from $356 / night

(1) Excellent 

24

Vacation condo with golf nearby in Sanibel Island

Southwest Gulf Coast / Sanibel Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
'' A STEP AWAY FROM THE BEACH '' is right on the beach , on the Gulf of Mexico , you step out the door and on to the beach , you can't get closer. This beautiful 1250 SQ.FT. ground floor , corner unit condo is well furnished with a light, bright and sunny ambiance. T …see more

from $213 / night

$1489 - $2838 / week

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from $213 / night

9

Apartment accommodation in Sanibel Island

Southwest Gulf Coast / Sanibel Island

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This excellent Timeshare waterfront resort is set on a west coast island that is world-renowned for its shelling beaches. This ground floor condo is located in Lighthouse Resort and Club --a luxury waterfront resort on the world top rated Sanibel Island, Florida . The s …see more

from $191 / night

$953 / week

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from $191 / night

18

Sanibel Island Vacation home rental

Southwest Gulf Coast / Sanibel Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Spacious apartment with 2 bedrooms and 2 bathrooms. Fully equipped kitchen with washer and dryer. Large living and dining area and balcony. Beach towels and chairs available. Free WiFi. Free Use of bicycles and tennis courts. Large pool with Jacuzzi. Complex on the …see more

from $203 / night

$1415 / week

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from $203 / night

24

Vacation condo with golf nearby in Sanibel Island

Southwest Gulf Coast / Sanibel Island

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
''DAYDREAMING'' BEACHFRONT condo is right on the Gulf of Mexico , you just can't get away from the beach . This beautiful one bedroom beach condo is tastefully furnished with a light , bright and sunny ambiance .The moment you walk through the door and see the beach you …see more

from $184 / night

$1288 - $1988 / week

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from $184 / night

21

Condo rental in Sanibel Island

Southwest Gulf Coast / Sanibel Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
Casa Ybel Resort beachfront resort on Sanibel Island has captivating views of the Gulf of Mexico. Furnished to feel like a private vacation home, your spacious suite features a separate living room with a sleeper sofa and a host of amenities, from complimentary Wi-Fi to …see more

from $273 / night

$1905 / week

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from $273 / night

19

Vacation home with swimming pool in Sanibel Island

Southwest Gulf Coast / Sanibel Island

3 6 28 nights min

  • 3 bedrooms
  • Sleeps 6
  • 28 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Location, location, location! A very, conveniently located 3 bedroom, 2 bathroom pool home just steps from West Gulf Drive's Beach Access #4! "Beach Time" is located in the most tranquil and desirable neighborhood on Sanibel directly off West Gulf Drive. The beach ac …see more

from $152 / night

$1062 - $2312 / week

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from $152 / night

25

Vacation apartment rental

Southwest Gulf Coast / Sanibel Island

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
This unit is located at the Sundial Beach Resort and is a spacious 3 bedroom, 2 bathroom condo that sits on the Gulf of Mexico with water views from the lanai. This condo offers over 1500 square feet of comfortable living space with a fully stocked kitchen and an open …see more

from $310 / night

$1590 - $2970 / week

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from $310 / night

(16) Very Good 

10

Vacation apartment in Sanibel Island

Southwest Gulf Coast / Sanibel Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
The Best Rate at Blind Pass on Bowman's Beach. A large, close to 1300 square foot apartment. The condominium is fully equipped with all linens, cooking utensils as well as all appliances. Decor is casual island style. King size bed in master bedroom, two twins in g …see more

from $128 / night

$895 - $1895 / week

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Responds fast!
avg. 3 hours 37 minutes

from $128 / night

(2) Excellent 

18

Vacation apartment in Sanibel Island

Southwest Gulf Coast / Sanibel Island

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Car not necessary
Welcome to our B23 family!!!!! When you stay at our condo, we like to think you’ve become a part of our family. Relax and enjoy our home as much as we do and learn why Sanibel Island is a true treasure. The condo itself offers a true home away from home experience thr …see more

from $221 / night

$1547 - $2400 / week

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from $221 / night

26

Vacation apartment with shared pool in Sanibel Island

Southwest Gulf Coast / Sanibel Island

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
A lovely 2 bedroom, 2 bathroom unit at Blind Pass Condominiums close to Bowman's Beach! Relax and unwind in this spacious and bright two bedroom, two bath, well appointed condo decorated in a tropical Sanibel style. The large, original wall mural will remind you of the …see more

from $202 / night

$1060 - $2260 / week

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from $202 / night

(6) Very Good 

38

Sanibel Island Vacation apartment rental

Southwest Gulf Coast / Sanibel Island

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Nearest beach 0.25 mi
  • Swimming pool
  • Child friendly
Enjoy your Sanibel vacation at the relaxing and quiet Breakers West complex in a unit that has seen many upgrades in the past year. This is a very spacious unit with 1,150 sq ft for you to relax in. The complex has a very private feel with only 18 units in the buildin …see more

from $205 / night

$1295 - $2705 / week

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Responds fast!
avg. 3 hours 39 minutes

from $205 / night

23

Vacation apartment with tennis court in Sanibel Island

Southwest Gulf Coast / Sanibel Island

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Beautifully decorated 4th floor unit with 2 bedrooms, 2 baths and queen sleeper sofa (sleeps 6). Bonus room with bumper pool and additional seating creates extra living space! Fully equipped eat-in kitchen, washer/dryer, screened-in lanai and a private penthouse sundec …see more

from $200 / night

$1400 - $2600 / week

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from $200 / night

(25) Very Good 

16

Vacation apartment in Sanibel Island

Southwest Gulf Coast / Sanibel Island

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Come and stay at our beautiful two bedroom Sanibel vacation condo! Our condo is perfect for families of four and offers one master bedroom and a second bedroom, ideal for two kids. There are also two full baths for your convenience and a nice living room with a tropical …see more

from $135 / night

$945 - $1435 / week

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from $135 / night

(2) Excellent 

21

Sanibel Island Vacation apartment rental

Southwest Gulf Coast / Sanibel Island

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Condominium - 2 Bedrooms, 2 Baths, Sleeps 4 - 6, bay views from every room! Designer refurbished - May, 2014 This is our family's second home and our favorite place to be! It is a 1450-square-foot, two-bedroom, two-bath, luxurious, eighth-floor condominium at the newl …see more

from $218 / night

$1529 - $2959 / week

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Responds fast!
avg. 3 hours 35 minutes

from $218 / night

11

Vacation condo in Sanibel Island

Southwest Gulf Coast / Sanibel Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
Welcome to Pointe Santo de Sanibel. One of our homes away from home can be your home also. B43 is a 4th floor penthouse with a private sundeck on the roof and B 5 is a 1st floor walkout to the beach. Both are professionally decorated, have the new open kitchens and marb …see more

from $397 / night

$2775 / week

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from $397 / night

(4) Very Good 

40

Sanibel Island Vacation apartment rental

Southwest Gulf Coast / Sanibel Island

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Swimming pool
If you love water views, the warm Florida sunshine, watching dolphins at play and manatees meandering this is the place for you! This Mariner Pointe ground level suite is a true water lover’s paradise. Amenities galore including tennis, fishing, swimming, boating (doc …see more

from $157 / night

$1095 - $2295 / week

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Responds fast!
avg. 1 hour 38 minutes

from $157 / night

(1) Excellent 

21

Vacation apartment with shared pool in Sanibel Island

Southwest Gulf Coast / Sanibel Island

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Sanibel's most unique and spectacular vacation condominium!! Truly the only one of its kind, this magnificent 3,000 square foot condominium with incredible gulf views!! Home has 3 Bedrooms, 3.5 bathrooms Master Bedroom suites (king, king, 2 queens) all with large priva …see more

from $293 / night

$2050 - $4045 / week

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from $293 / night

(1) Excellent 

20

Sanibel Island Vacation home rental

Southwest Gulf Coast / Sanibel Island

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Our home is located in The Dunes, a semi-private golf course community with club house, pro shop, community pool, tennis court, & restaurant all within a quarter mile. It is conveniently located about 300 yards from the bay beach and about a 5 minute bike ride from the …see more

from $130 / night

$975 - $2125 / week

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Responds fast!
avg. 3 hours 32 minutes

from $130 / night

25

Vacation apartment rental

Southwest Gulf Coast / Sanibel Island

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
This spectacular 1 bedroom condo is located at the Sundial Beach Resort and is the perfect spot to call home while vacationing in paradise. This unit has been totally updated and dressed with all new furniture to compliment the beachy setting of Sanibel Island. The sh …see more

from $207 / night

$966 - $1970 / week

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from $207 / night

(1) Excellent 

21

Sanibel Island Vacation apartment rental

Southwest Gulf Coast / Sanibel Island

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
This 3 bedroom 2 bath unit will please your every need while staying on Sanibel Island. A spiral staircase on the porch takes you down to a screened in cabana area. Perfect for those bikes, beach chairs and children's beach toys...............Sundial East & West Condom …see more

from $223 / night

$1562 - $3161 / week

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from $223 / night

(19) Very Good 

20

Vacation villa in Sanibel Island

Southwest Gulf Coast / Sanibel Island

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Each of our four spacious Villas is fully equipped to make your vacation stay comfortable and effortless. Each Villa offers over 1200 square feet of air conditioned living area and features two bedrooms and 1 & 1/2; baths, fully appointed kitchens, separate living and d …see more

from $170 / night

$1050 - $1610 / week

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from $170 / night

27

Vacation home with swimming pool in Sanibel Island

Southwest Gulf Coast / Sanibel Island

3 10 28 nights min

  • 3 bedrooms
  • Sleeps 10
  • 28 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Don't miss out on this newly built 3 bedroom, 2 bathroom pool home situated in the quiet and secluded Sanibel Golf Club community. "Calypso Tides" is a new construction completed in December 2016, equipped with all the bells and whistles you could hope for in your next …see more

from $152 / night

$1062 - $2438 / week

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from $152 / night

64

Home rental in Sanibel Island

Southwest Gulf Coast / Sanibel Island

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
The Sanctuary home is situated in Sanibel's exclusive Sanctuary Golf Community, this 6,000 sq. ft. 5 bedroom, 6 bath home is the perfect choice for a luxurious tropical retreat. Soaring high ceilings and a sprawling, multi-level pool deck with spa overlooking 2 fairways …see more

from $400 / night

$2800 / week

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from $400 / night

(8) Excellent 

10

Home rental in Sanibel Island with shared pool

Southwest Gulf Coast / Sanibel Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Enjoy the spectacular views from this direct Gulf front condo overlooking beautiful natural native vegetation of seagrapes, sea oats, and palm trees then out to the beach where warm waters wash up on Sanibel's 15 miles of beautiful uninterrupted shell filled beaches. As …see more

from $250 / night

$1400 - $3100 / week

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from $250 / night

(5) Excellent 

24

Vacation apartment in Sanibel Island

Southwest Gulf Coast / Sanibel Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Stunning Sophistication on Sanibel Island! Welcome to Sand Pointe #214, or as it is commonly called, "Sanibel Blue Lagoon", where you can enjoy all that Sanibel has to offer in style in this Gulf-Front condominium. Here the pace is relaxed and the beaches private. Pro …see more

from $172 / night

$1200 - $3000 / week

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Responds fast!
avg. 1 hour 9 minutes

from $172 / night

29

Vacation home with swimming pool in Sanibel Island

Southwest Gulf Coast / Sanibel Island

3 6 28 nights min

  • 3 bedrooms
  • Sleeps 6
  • 28 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
WOW!! The expansive views from this home will keep you speechless and in awe of the true beauty that this spectacular home (and island!) have to offer. The Woodring Bayhouse boasts 3 bedroom & 3.5 bathrooms and some of the most luxurious living accommodations on one of …see more

from $225 / night

$1575 - $3325 / week

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from $225 / night

(2) Very Good 

13

Sanibel Island Vacation apartment rental

Southwest Gulf Coast / Sanibel Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
Sundial E-210 is a fabulous Gulf front two bedroom two bath fully equipped condominium. This condo has been recently re-modeled and has all the creature comforts of home. Take a running jump off the beach front lanai and you are on the beach or watch the Dolphins and …see more

from $240 / night

$1679 - $3403 / week

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from $240 / night

16

Apartment rental in Sanibel Island

Southwest Gulf Coast / Sanibel Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
Pointe Santo is a beautifully landscaped property centered around a peaceful lagoon on the Gulf of Mexico. This comfortable 2 bedroom, 2 bathroom condo is located on the second floor with a view over the landscaped lagoon out to the beach. 3 flat screen TV's. The condo …see more

from $158 / night

$1104 - $2674 / week

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from $158 / night

(10) Very Good 

13

Home accommodation in Sanibel Island

Southwest Gulf Coast / Sanibel Island

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Ask about children
  • Air conditioning
There are only 7 cottages that make up this quiet Gulf access neighborhood. There is an on-site laundry facility and is conveniently located to bike paths, restaurants, shops and only a 3 minute walk across the street to the sugary white shell-filled beaches. This SMOKE …see more

from $125 / night

$700 - $1701 / week

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from $125 / night

22

Sanibel Island Vacation home rental

Southwest Gulf Coast / Sanibel Island

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
This beautiful 4 bedrrom 4 1/2 bath home is located in Beachview Estates (BirdieView) The home overlooks one of the nicest golf courses on Sanibel and a gorgeous lake. Relax in the large screen enclosed, heated pool. Beautifully furnished - this 2 story, 3500 square …see more

from $279 / night

$1953 / week

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from $279 / night

21

Vacation apartment in Sanibel Island

Southwest Gulf Coast / Sanibel Island

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Ask about pets
Sparkling Views from this two bedroom, two bathroom Gulf Front condo. If you are looking for a great location with beautiful views of the Gulf and beach this is the condo for you. While this second floor condo has older furnishings, original kitchen and bathrooms, …see more

from $225 / night

$1575 - $3350 / week

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from $225 / night

(15) Excellent 

109

Vacation apartment rental

Southwest Gulf Coast / Sanibel Island

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Island Beach Club, 2265 WestGulf Drive, Sanibel. Beautiful ocean view penthouse level condominium located in the Island Beach Club next to exculsive Casa Ybel Resort on upscale West Gulf Drive. 2 bedrooms with ensuite baths. (great for couples or families) Beautifu …see more

from $185 / night

$2400 - $2600 / week

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Responds fast!
avg. 1 hour 44 minutes

from $185 / night

30

Vacation home with swimming pool in Sanibel Island

Southwest Gulf Coast / Sanibel Island

3 6 28 nights min

  • 3 bedrooms
  • Sleeps 6
  • 28 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Welcome to "Down Time", a true classic beach cottage that's been newly renovated to be the fresh, clean & comfortable modern escape that you have been searching for in your next Sanibel rental home! This beachside beauty boasts new hardwood floors throughout, an open fl …see more

from $163 / night

$1138 - $1563 / week

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from $163 / night

26

Vacation apartment in Sanibel Island

Southwest Gulf Coast / Sanibel Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
Loggerhead Cay 234 is a top floor, well appointed two bedroom two bath pool view condo. Loggerhead Cay is one of the most popular family friendly complexes on Sanibel. Its East End Gulf front location makes for easy on and off the Island as well as being very close t …see more

from $137 / night

$956 - $2188 / week

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from $137 / night

15

Vacation apartment in Sanibel Island

Southwest Gulf Coast / Sanibel Island

3 8 14 nights min

  • 3 bedrooms
  • Sleeps 8
  • 14 nights min
  • Ask about children
Spacious, three bedroom, two bath second floor condominium. This is direct beach front with fabulous views of the Gulf of Mexico. 2 flat screen TV's. Junonia is located on West Gulf Dr. and is a small 8 unit condominium complex complete with a large pool and clubhous …see more

from $276 / night

$1931 - $4167 / week

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from $276 / night

1