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Summerland Key vacation rentals

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Top-rated vacation rentals in Summerland Key

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Cottage in Cudjoe Key

4.91 out of 5 average rating, 133 reviews

ATLANTIS...Ocean Front Cottage Retreat!

ATLANTIS~An ocean front cottage retreat! Completely remodeled, direct ocean-front cottage offers everything you'll need for the perfect getaway. Boat dock (25ft), HD TVs, washer & dryer, S/S appliances & gas cooking! Complimentary kayaks & bikes plus access to all the Venture Out Residential Condominium Community amenities: heated pool, Jacuzzi, kiddie pool, tennis, basketball & bocce courts, ocean bay swimming area, marina w/fuel, boat ramps & wash station, and a convenience market on-site!

Mar 2 – 9

G$181,881 GYD per night

Home in Key West

4.94 out of 5 average rating, 272 reviews

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!

Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV (bring your Netflix, Amazon UN/PW's). Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.

Sep 20 – 27

G$104,907 GYD per night

Guest suite in Marathon

4.98 out of 5 average rating, 185 reviews

Casa Mariposa: Easy walk to Sombrero Beach

Book your relaxing getaway now at Casa Mariposa in the heart of the Florida Keys! See why we were rated a top 15 cozy retreat in the Keys, 1 0f 24 amazing AirBNB rentals in the Keys, and, in 2023, 1 of 23 Amazing Airbnbs In Florida Keys. Step out from your private suite to our 50' lap pool surrounded with tropical foliage, large patio, and tropical gardens. Avoid beach parking fees with a short walk from your suite at Casa Mariposa! Contact us if you are interested in other lengths of stay.

Oct 12 – 19

G$45,412 GYD per night

Tiny home in Big Pine Key

4.8 out of 5 average rating, 89 reviews

Breezy pines 28 foot 5th wheel trailer .

Central air,queen size bed in the bedroom,queen size futon in the living room, tv,stove,refrigerator,propane grill,wifi,and an outdoor dining table.Owner uses the outdoor storage shed for fishing purposes.Newly renovated vinyl floor.New carpet in the bedroom.New toilet installed.The water pressure has been fixed and is now perfect.One cup k cup machine.Mile marker 30.Take the north entrance.Take your first left.Take your second right.Bare right and lot 54 is the first trailer on the left.

Jun 2 – 9

G$24,674 GYD per night

Home in Cudjoe Key

4.9 out of 5 average rating, 104 reviews

Sunrise Beach Escape

For your next vacation, come stay in this resort home, where you'll enjoy a cocktail at sunset alongside the Cudjoe bay overlooking the Atlantic Ocean. This beautiful and luxurious home is part of the Sunrise Beach Resort, an exclusive 11 home gated community overlooking the Atlantic Ocean & Cudjoe Bay. A community that is only 17 miles north of Key West. Make yourself at home in this tastefully decorated 1200 sq foot living space, which offers countless amenities such as kayaks and bikes.

Jan 17 – 24

G$83,510 GYD per night

Cottage in Little Torch Key

4.91 out of 5 average rating, 146 reviews

Waterfront Cozy Cottage with Boat Ramp & Dock!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with 250 foot dock, ramp, and basin for your boat. It's a must-see rustic outdoor environment and fishery experience, very typical in the Keys! The property lot is almost an acre with a work section and still very spacious. Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the dock and enjoy the underwater scenery!

Apr 25 – May 2

G$113,080 GYD per night

Boat in Islamorada

4.92 out of 5 average rating, 327 reviews

360 DEGREE WATERVIEW HOUSEBOAT

IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.

Jan 28 – Feb 4

G$39,075 GYD per night

Guesthouse in Key West

4.93 out of 5 average rating, 527 reviews

Old Town - Room Opens to Pool and Garden

Located in the heart of Old Town, we are three blocks from Duval Street, a 10-minute walk to Higgs Beach, and around the corner from the best, least-expensive meal in town--El Siboney Cuban Restaurant. We suggest bicycling around Key West. Rentals from We-Cycle Bike Shop can be delivered to our door. Two blocks away, The Duval Loop offers free air-conditioned bus service 7 a.m. until midnight. We also offer a link with recommendations for excursions, tours, & restaurants.

Jun 8 – 15

G$70,576 GYD per night

Home in Cudjoe Key

4.97 out of 5 average rating, 121 reviews

Cudjoe Key Home with a View

We are so excited to share our little piece of paradise with you! Our unit is located a short walk away from all the amenities the Venture Out community has to offer such as a pool, hot tub, lagoon, bocce ball, tennis courts, playground and boat marina. On the property we have a 2-person hybrid kayak for your enjoyment. We also provide table games (we love a game night) as well as the equipment to play bocce ball and darts which can be played in the recreation center.

Oct 7 – 14

G$76,030 GYD per night

Apartment in Key West

4.92 out of 5 average rating, 1036 reviews

At Mine | Lovely Suite steps from Duval Street

Beautifully renovated boutique hotel suite steps from Duval Street. This property is situated on a quiet street and offers a private pool and peaceful accommodation for vacationers and business travelers. The unit features a comfortable Queen-sized bed, Mini Fridge, a microwave, Iron and iron board, hangers, TV, and AC. Indulge in Key West's warm weather year-round. This special place is close to everything, making it easy to plan your visit.

Jul 28 – Aug 4

G$59,356 GYD per night

Home in Cudjoe Key

4.92 out of 5 average rating, 142 reviews

Paradise and Cudjoe Bay

"This three-story home overlooks the Atlantic ocean in a gated community of only 10 other homes. Just south enough to enjoy the bluest water in the keys and only 20 minutes away from Key West! This pristine home sleeps 6 comfortably and makes a great destination to exploring all the wonders the FL Keys. Come enjoy the pool, fishing, boating, diving or just relax with the ocean breeze. This location has all the best of the Keys."

Jan 11 – 18

G$84,564 GYD per night

Home in Cudjoe Key

4.94 out of 5 average rating, 17 reviews

May Extravaganza - Relax in Paradise!

Wow!!! Our new spacious 3 bedrooms, 2 full bath home on a 60-foot wide, deep-water canal with a 60-foot-long dock is only 1,500 feet from the open waters of Kemp Channel. Our canal enters Kemp Channel just to the north of the Overseas Highway Bridge, so that our guests bringing their boats have access to the Atlantic Ocean and the Gulf of Mexico. We have a guest friendly cancellation policy as described below in this listing.

Oct 1 – 8

G$46,948 GYD per night

Vacation rentals for every style

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Popular amenities for Summerland Key vacation rentals

Laptop-friendly workspace

Stay near Summerland Key's top sights

Square Grouper Bar and Grill47 locals recommend

Tonio's Seafood Shack & Tiki Bar14 locals recommend

Galley Grill19 locals recommend

My New Joint27 locals recommend

Murray's Market16 locals recommend

Cudjoe Sales Fishermen's Warehouse4 locals recommend

Other great vacation rentals in Summerland Key

Apartment in Big Pine Key

4.86 out of 5 average rating, 7 reviews

Apartment in Big Pine

Mar 3 – 10

G$40,773 GYD per night

Home in Summerland Key

4.83 out of 5 average rating, 6 reviews

Bungalows at Sugarloaf Beach - Little Hammock

May 18 – 25

G$95,243 GYD per night

Home in Cudjoe Key

4.86 out of 5 average rating, 43 reviews

*Emerald Seas*-Florida Keys Ocean Front Paradise!

Oct 10 – 17

G$102,037 GYD per night

Home in Cudjoe Key

5.0 out of 5 average rating, 23 reviews

Paradise in Cudjoe! Perfect Family Home!

Oct 4 – 11

G$80,632 GYD per night

Camper/RV in Big Pine Key

4.92 out of 5 average rating, 37 reviews

Delightful 1 bedroom camper with pool

Jun 9 – 16

G$35,854 GYD per night

Cottage in Cudjoe Key

4.91 out of 5 average rating, 79 reviews

King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks

Sep 25 – Oct 2

G$95,829 GYD per night

Home in Cudjoe Key

4.86 out of 5 average rating, 28 reviews

Keys Island Villa - Venture Out Home 354

Sep 30 – Oct 7

G$84,360 GYD per night

Condo in Key West

4.99 out of 5 average rating, 84 reviews

Hidden Beach Duplex, Best Place in Key West

Aug 3 – 10

G$144,949 GYD per night

Other great vacation rentals in Summerland Key

Home in Marathon

5.0 out of 5 average rating, 16 reviews

Horizon

Aug 31 – Sep 7

G$168,443 GYD per night

Home in Cudjoe Key

4.95 out of 5 average rating, 19 reviews

Conch Cabana in Paradise 23 miles outside Key West

Apr 15 – 22

G$83,286 GYD per night

Home in Cudjoe Key

4.95 out of 5 average rating, 22 reviews

White Vacation Home. Free cancellation see details

Apr 12 – 19

G$144,420 GYD per night

Home in Cudjoe Key

4.82 out of 5 average rating, 49 reviews

Spanish Queen @Venture Out

Aug 18 – 25

G$80,050 GYD per night

Camper/RV in Big Pine Key

4.89 out of 5 average rating, 45 reviews

You’re on island time at The Island Girl

Aug 25 – Sep 1

G$40,680 GYD per night

Home in Marathon

4.97 out of 5 average rating, 33 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

Apr 26 – May 3

G$130,207 GYD per night

Vacation home in Cudjoe Key

5.0 out of 5 average rating, 37 reviews

Beautiful Cottage & Amenities in Gated Community

Dec 20 – 27

G$79,579 GYD per night

Home in Cudjoe Key

5.0 out of 5 average rating, 7 reviews

Venture Out- Million Dollar Island Resort

Nov 30 – Dec 7

G$65,552 GYD per night

Quick stats about vacation rentals in Summerland Key

Total rentals
210 properties
Rentals with a pool
140 properties have a pool
Pet-friendly rentals
80 properties allow pets
Family-friendly rentals
170 properties are a good fit for families
Total number of reviews
3.5K reviews
Nightly prices starting at
G$22,999 GYD before taxes and fees

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Summerland Key?
Yes! Work meets play with ease at over 80 vacation rentals in Summerland Key featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Summerland Key?
Four-legged friends are welcome in Summerland Key. Choose from more than 80 vacation rentals for guests traveling with pets.
How much does it cost to stay in campsite rentals in Summerland Key?
Experience the best of Summerland Key with our campsite rentals, starting at about $110 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Summerland Key have self check-in?
Absolutely! We offer over 30 house rentals with self check-in in Summerland Key. Enjoy a tailored experience with all the comforts you desire.
Are there Summerland Key house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 100 house rentals with pools in Summerland Key, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Summerland Key have a bbq area?
Absolutely! We offer over 60 house rentals with a bbq area in Summerland Key. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Summerland Key have wifi?
Absolutely! We offer over 10 cottage rentals with wifi in Summerland Key. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Summerland Key?
Summerland Key has more than 150 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore