50 Best Sanibel Island Vacation rentals on Holiday Lettings - Cottages

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2,272 Vacation rentals

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 $215 / night

$1,073 / week

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from $215 / 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

$1,488 - $3,338 / week

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from $213 / night

(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

$1,200 - $2,000 / week

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from $150 / night

(4) 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

$1,488 - $3,338 / week

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from $213 / night

(3) Excellent 

26

Condo rental in Sanibel Island with golf nearby

Southwest Gulf Coast / Sanibel Island

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
This spacious (1500 sq ft) ground floor condo has been recently remodelled. It provides superb accommodation, sleeping up to 6 people in 3 bedrooms with 2 full bathrooms. Secure wi-fi is avalable in the condo. The condo is in an ideal island location - situated only a …see more

from $129 / night

$900 - $1,900 / week

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from $129 / 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
  • Swimming pool
  • Child friendly
''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 $142 / night

$988 - $2,191 / week

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from $142 / night

28

Sanibel Island Vacation home rental

Southwest Gulf Coast / Sanibel Island

4 10 30 nights min

  • 4 bedrooms
  • Sleeps 10
  • 30 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
A classic wooden Floridian house and guest house set on stilts in an acre of sub-tropical landscaped garden. Large outdoor, private, secluded raised pool with an expansive decking area consisting of a four-seater hot tub, recreation area and six sun beds. Five minutes w …see more

from $286 / night

$2,002 / week

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Responds fast!
avg. 2 hours 37 minutes

from $286 / night

24

Home rental in Sanibel Island with golf nearby

Southwest Gulf Coast / Sanibel Island

5 9 Min stay varies

  • 5 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 $500 / night

$3,500 - $3,850 / week

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from $500 / 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 $200 / night

$1,398 / week

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from $200 / night

(30) Very Good 

16

Vacation apartment in Sanibel Island

Southwest Gulf Coast / Sanibel Island

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • 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 - $1,435 / week

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from $135 / night

28

Home rental in Sanibel

Sanibel Island / Sanibel

3 6 28 nights min

  • 3 bedrooms
  • Sleeps 6
  • 28 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Secluded Tropical Paradise- Secret Harbour! Set on two canals this three bedroom two bathroom pool home is the perfect spot to truly get away from it all! Walk into the open, colorful living room with vaulted ceilings, comfortable couch, flat screen television and tropi …see more

from $236 / night

$1,652 / week

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from $236 / night

25

Sanibel Island Vacation home accommodation

Southwest Gulf Coast / Sanibel Island

3 6 28 nights min

  • 3 bedrooms
  • Sleeps 6
  • 28 nights min
  • Ask about children
1593 Sand Castle -Elegance in the Dunes Golf and Tennis Club Community. Be swept away each day with the golf course views and blue skies from your home away from home. An outstanding and meticulously maintained 3 bedroom, 2.5 bath duplex home with all the custom details …see more

from $183 / night

$1,281 / week

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from $183 / night

27

Vacation apartment rental

Southwest Gulf Coast / Sanibel Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
This nice unit has two bedrooms and two baths. 2 flat screen TV's. The unit offers views of the center courtyard area. Amenities include pool, tennis, BBQ, and shufflelboard. Loggerhead Cay is a 168 unit complex located directly on the beach near the entrance to Sa …see more

from $148 / night

$1,033 - $2,310 / week

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from $148 / night

(23) Excellent 

Certificate of Excellence

102

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 exclusive Casa Ybel Resort on upscale West Gulf Drive. 2 bedrooms with ensuite baths. (great for couples or families) Beautifu …see more

Certificate of Excellence

from $200 / night

$2,800 / week

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Responds fast!
avg. 1 hour 38 minutes

from $200 / night

22

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
This is a wonderful ground floor, 2 bedroom 2 bath unit, close to the BBQ area and tennis courts. This unit has a bright tropical Florida theme. 3 Flat screen TV's. It is situated close to many shops and restaurants. Overlooks a beautifully landscaped courtyard …see more

from $143 / night

$1,004 - $2,188 / week

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from $143 / night

(2) Excellent 

21

Sanibel Island Vacation apartment rental

Southwest Gulf Coast / Sanibel Island

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
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 $422 / night

$2,959 / week

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from $422 / night

25

Sanibel Island Vacation condo rental

Southwest Gulf Coast / Sanibel Island

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Sanibel Arms West is a deluxe, beachfront condominium resort located right on the Gulf of Mexico with world famous white sand beaches. This spacious, two bedroom, vacation rental is perfect for families or groups offering all the amenities of home just yards from the be …see more

from $185 / night

$1,250 - $2,675 / week

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Responds fast!
avg. 48 minutes

from $185 / night

(3) Excellent 

42

Vacation home with golf nearby in Sanibel Island

Southwest Gulf Coast / Sanibel Island

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
The Sand Castle, as we lovingly call our vacation house, is a beautiful single-family 3 bedroom / 2 bath luxury vacation house with magnificent views overlooking the greens and lakes of The Dunes, an 18-hole championship golf course and tennis club. The house has a la …see more

from $300 / night

$2,000 - $3,500 / week

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Responds fast!
avg. 3 hours 12 minutes

from $300 / night

(1) Very Good 

20

Vacation apartment in Sanibel Island

Southwest Gulf Coast / Sanibel Island

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
30 Steps to beautiful white sand beaches! This charming two bedroom two bathroom, first floor condo is the perfect spot for a great beach vacation. The older, open kitchen has everything you need to create a great meal or heat up leftovers from a fabulous restaurant. …see more

from $229 / night

$1,603 / week

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from $229 / night

15

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
This very nice 2 bedroom/2 bath unit is located on the 2nd floor and has wonderful tropical views. This property offers lush grounds with lake and club house island. Amenities include 2 tennis courts, a swimming pool, whirlpool and BBQ areas. A great family place …see more

from $191 / night

$1,338 - $2,917 / week

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from $191 / night

21

Apartment rental in Sanibel Island with shared pool

Southwest Gulf Coast / Sanibel Island

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Bay Front Views from this newly remodeled two bedroom two bathroom Mariner Point condo. Have the best of both worlds with amazing views from your lanai and a large canal in the back. Granite counters and stainless steel appliances will inspire you to create gourmet me …see more

from $145 / night

$1,015 / week

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from $145 / night

22

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
This cute, tropical 2 bedroom 2 bath, ground floor unit offers easy access to the pool. 3 flat screen TV's. The unit offers views of the center courtyard and pool area. Other amenities include tennis, BBQ, and shuffleboard. Loggerhead Cay is a 168 unit complex …see more

from $143 / night

$1,004 - $2,188 / week

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from $143 / night

(3) Very Good 

25

Apartment rental in Sanibel Island

Southwest Gulf Coast / Sanibel Island

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
Secluded three bedroom three bath Gulf Front Townhouse. Seagrape Village is a small four unit complex (2 duplexes). This East end townhouse complex has a large pool and is just a short distance to shopping and restaurants. It does not get any better than this. Come on d …see more

from $252 / night

$1,764 - $3,282 / week

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from $252 / night

(2) Excellent 

25

Vacation condo in Sanibel Island

Southwest Gulf Coast / Sanibel Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.05 mi
  • Swimming pool
You'll have a beautiful ocean and beach view in cozy surroundings here in A21, whether you're preparing morning coffee in the kitchen, enjoying that cup on the lanai, curled up on an overstuffed sofa, or continuing to doze comfortably in your king-sized bed. Please not …see more

from $193 / night

$1,350 - $3,707 / week

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Responds fast!
avg. 56 minutes

from $193 / night

22

Apartment rental in Sanibel Island

Southwest Gulf Coast / Sanibel Island

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Don’t miss this well-kept beachside Sanibel condo in Loggerhead Cay. This two bedroom two bath condo has everything you need for a great family vacation. Enjoy the well equipped kitchen to create great family meals or just heat up leftovers from your favorite restaur …see more

from $157 / night

$1,099 / week

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from $157 / night

17

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
This very nice condo is located on the ground floor and consists of a living room, dining room and fully equipped kitchen. The bedding is a King in the master, & full & twin in the guest. Courtyard view with a peek of the gulf. 3 flat screen TV's. Loggerhead Cay h …see more

from $143 / night

$1,004 - $2,188 / week

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from $143 / night

22

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 hosts 168 2 bedroom, 2 bathroom condos on Sanibel's east end. This very nice condo is located on the 4th floor and consists of a living room, dining room and fully equipped kitchen. The bedding is a King in the master, & full and twin in the guest. 2 …see more

from $137 / night

$956 - $2,188 / week

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from $137 / night

20

Sanibel Island Vacation home rental

Southwest Gulf Coast / Sanibel Island

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning
Relax among the tropical sights and sounds in this charming Duggars Tropical Village Cottage. Bright beachy décor greet you in this one bedroom one bathroom bungalow. The comforting living room features a flat screen TV, comfy pull out sleeper sofa and sliding glass d …see more

from $126 / night

$882 / week

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from $126 / night

16

Vacation apartment 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
Beachfront complex, heated pool, less than 100 steps to the beach, a spacious condo with cathedral ceilings and a loft. All of this makes up your perfect vacation home. Walk into the bright and airy condo with soaring ceiling, tropical views and ample room for your fa …see more

from $141 / night

$987 / week

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from $141 / night

(1) Excellent 

21

Apartment rental 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
  • Child friendly
Beautiful ground floor condo with access to 2 beaches. Walk across the street and you're on the magnificent, white sand beaches of the Gulf of Mexico, or, walk to the end of the Lighthouse Point property and you're on the Bay beach with pier, jetty and the historic …see more

from $136 / night

$950 / week

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from $136 / night

(18) Excellent 

26

Vacation condo in Sanibel Island

Southwest Gulf Coast / Sanibel Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.3 mi
  • Swimming pool
It is a little-known fact that Blind Pass is the closest condo complex to Bowman's Beach, one of the top 10 beaches in the world, according to US News Travel, on Sanibel Island, which is Frommer's favorite destination in the world. This spacious, light and airy dwelli …see more

from $147 / night

$1,025 - $1,995 / week

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from $147 / night

15

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
This Pointe Santo vacation condo is located in one of Sanibel Island's most popular vacation spots. The grounds surrounding our condo are quite beautiful, and the complex even offers special programs for children at little or no cost. Our condo is on the ground floor, s …see more

from $248 / night

$1,737 - $3,473 / week

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from $248 / night

25

Vacation condo in Sanibel Island

Southwest Gulf Coast / Sanibel Island

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Sanibel Arms West is a deluxe, beachfront condominium resort located right on the Gulf of Mexico with world famous white sand beaches. This spacious, two bedroom, vacation rental is perfect for families or groups offering all the amenities of home just yards from the be …see more

from $185 / night

$975 - $2,350 / week

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Responds fast!
avg. 48 minutes

from $185 / night

23

Sanibel Island Vacation home rental

Southwest Gulf Coast / Sanibel Island

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Ask about children
  • Air conditioning
Relax among the tropical sights and sounds in this charming Duggars Tropical Village Cottage. Vaulted cross beam ceilings give this one bedroom beach bungalow a spacious open feeling. The comfortable living room features a flat screen TV, comfy striped sofa, a beautif …see more

from $126 / night

$882 / week

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from $126 / night

(6) Excellent 

33

Sanibel Island Vacation home rental

Southwest Gulf Coast / Sanibel Island

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Come relax and enjoy paradise in this stylishly updated condominium in one of Sanibel's best locations. Professionally decorated in charming island style, this is the ideal tropical retreat to make your vacation getaway perfect. Open the doors on the lanai, and you will …see more

from $257 / night

$1,700 - $3,300 / week

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from $257 / night

24

Vacation apartment in Sanibel Island

Southwest Gulf Coast / Sanibel Island

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
This nice condo is located on the second floor with a view over the pool and courtyard out to the Gulf of Mexico. A very good value! The bedding is a king in the master, two twins in the guest and a sleeper sofa in the livingroom. 2 flat screen TV's. The condo sleep …see more

from $171 / night

$1,200 - $2,188 / week

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from $171 / night

(2) Excellent 

23

Vacation apartment rental

Southwest Gulf Coast / Sanibel Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
Pointe Santo D-5 is a wonderful two bedroom two bath ground floor walkout. Walk right out your screened lanai to the beautiful courtyard path to the beach. Condo comes fully equipped with everything needed for a memorable Sanibel Vacation. Stay one night here you will n …see more

from $232 / night

$1,621 - $2,894 / week

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from $232 / night

30

Vacation home in Sanibel Island

Southwest Gulf Coast / Sanibel Island

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
Beach side four bedrooms, three bathroom home available for weekly rentals. This charming older house is like a step back in time to Old Sanibel. This bungalow was one of the first homes built on Sanibel and was a Sears and Roebuck kit home. This home has older finis …see more

from $314 / night

$2,198 / week

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from $314 / night

27

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
This comfortable third floor unit has two bedrooms and two baths The unit offers views of the center courtyard and pool. 3 TV's, 2 are flat screens. Wireless internet. Other amenities include wireless internet,tennis, BBQ, and shuffleboard. Loggerhead Cay is a 168 …see more

from $156 / night

$1,094 - $2,188 / week

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from $156 / night

(4) Excellent 

21

Sanibel Island Vacation home rental

Southwest Gulf Coast / Sanibel Island

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Enjoy the gorgeous views of San Carlos Bay in this 2 bedroom/2 bathroom condominium! You can watch the dolphins and manatees play, the fish jumping and the birds diving right from your private screened balcony! This condo is decorated in splashes of seafoam greens and f …see more

from $185 / night

$850 - $1,850 / week

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from $185 / night