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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Superhost

Cottage in Cudjoe Key

4.92 out of 5 average rating, 132 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!

Dec 16 – 23

G$181,800 GYD per night

Guest favorite

Guest suite in Marathon

4.98 out of 5 average rating, 184 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.

Jul 4 – 11

G$45,391 GYD per night

Superhost

Tiny home in Big Pine Key

4.8 out of 5 average rating, 88 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.

Sep 7 – 14

G$22,926 GYD per night

Superhost

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.

Sep 6 – 13

G$83,472 GYD per night

Guest favorite

Home in Ramrod Key

5.0 out of 5 average rating, 6 reviews

Canalfront 3BD/2BA|FLKeys|POOL|DOCK

Welcome to Casa Sirena, a canal-front paradise home in the peaceful lower Florida Keys. Enjoy the island breeze as soon as you arrive. You can enjoy a game of pool or sit & relax. Walk upstairs and catch sunset views from the outdoor balcony leading into the main entrance of the home. The Kitchen island offers additional seating for your guests along side the Dining Room table. Coffee lovers can enjoy a coffee station in the kitchen. Family kid games in the living room entertainment center.

Mar 7 – 14

G$63,869 GYD per night

Guest favorite

Cottage in Little Torch Key

4.91 out of 5 average rating, 145 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!

Sep 14 – 21

G$99,900 GYD per night

Superhost

Villa in Marathon

4.89 out of 5 average rating, 144 reviews

New Aqua Lodge 2Beds 1 Bath with Full Kitchens

This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!

Jan 29 – Feb 5

G$86,463 GYD per night

Guest favorite

Home in Cudjoe Key

4.97 out of 5 average rating, 119 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.

Sep 18 – 25

G$60,835 GYD per night

Superhost

Home in Cudjoe Key

4.81 out of 5 average rating, 220 reviews

OCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!

*PERFECT LOCATION! * 35' Seawall *AWWSOME 2 bedroom 2 full bath waterfront stilted house in Cudjoe Key. Located in the lower Florida Keys at MM# 23 only 25minutes to Key West. Located in the gated community of Venture Out Resort. *Sleeps 6 *55" TV *A/C & heat *Fully equipped kitchen *Brand New Amenities including grill, 4 Bikes & 2 two-person Kayaks *PLUS: Pool, HotTub, Marina, Boat Ramp, Store, Playground, Game Room, Tennis, Library, etc. Too much to list!

Dec 14 – 21

G$89,082 GYD per night

Guest favorite

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$46,928 GYD per night

Superhost

Home in Cudjoe Key

4.88 out of 5 average rating, 188 reviews

Newly Renovated Oceanside House with Pool

This home is on the Atlantic side of US 1. It is part of Sunrise Beach Resort, a gated community built in 2007 with only 10 other homes. Lounge in your private hammock or enjoy the gorgeous tropical landscaping and cool breezes on one of two balconies, dock or poolside, where you can soak up the sun steps from the house. Breathtaking southwest views of the blue-green ocean and sunsets can be seen from the pool and dock.

Nov 9 – 16

G$85,719 GYD per night

Guest favorite

Guest suite in Marathon

5.0 out of 5 average rating, 162 reviews

Dolphin Drive

Spacious, fun unit with private entrance and large living room with kitchen, bedroom and bathroom (Sleeps up to 4). Game room/living room includes billiards, ping pong and darts. Room for your boat trailer and vehicle in long, private driveway. 2/10 of a mile from the public boat ramp.

May 14 – 21

G$30,980 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Summerland Key vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

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

Guest favorite

Camper/RV in Big Pine Key

4.92 out of 5 average rating, 39 reviews

Having fun in the lower Keys

Aug 28 – Sep 4

G$34,410 GYD per night

Guest favorite

Camper/RV in Big Pine Key

4.92 out of 5 average rating, 36 reviews

Delightful 1 bedroom camper with pool

Jun 26 – Jul 3

G$35,838 GYD per night

Guest favorite

Home in Cudjoe Key

5.0 out of 5 average rating, 22 reviews

Paradise in Cudjoe! Perfect Family Home!

Oct 4 – 11

G$80,563 GYD per night

Superhost

Home in Cudjoe Key

4.86 out of 5 average rating, 42 reviews

*Emerald Seas*-Florida Keys Ocean Front Paradise!

Aug 4 – 11

G$143,490 GYD per night

Guest favorite

Cottage in Cudjoe Key

4.91 out of 5 average rating, 77 reviews

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

Oct 5 – 12

G$106,008 GYD per night

Superhost

Home in Cudjoe Key

4.86 out of 5 average rating, 28 reviews

Keys Island Villa - Venture Out Home 354

Nov 30 – Dec 7

G$88,888 GYD per night

Superhost

Home in Cudjoe Key

4.85 out of 5 average rating, 47 reviews

Spanish Queen @Venture Out

Jun 22 – 29

G$80,015 GYD per night

Guest favorite

Home in Cudjoe Key

4.95 out of 5 average rating, 19 reviews

Conch Cabana in Paradise 23 miles outside Key West

Nov 29 – Dec 6

G$63,931 GYD per night

Show all

Other great vacation rentals in Summerland Key

Superhost

Home in Cudjoe Key

5.0 out of 5 average rating, 7 reviews

Venture Out- Million Dollar Island Resort

Jun 29 – Jul 6

G$65,523 GYD per night

Guest favorite

Vacation home in Cudjoe Key

5.0 out of 5 average rating, 35 reviews

Beautiful Cottage & Amenities in Gated Community

Oct 7 – 14

G$64,525 GYD per night

Guest favorite

Campsite in Cudjoe Key

5.0 out of 5 average rating, 8 reviews

Little Palm By The Sea- RV Site, Cudjoe Key Fl.

Aug 25 – Sep 1

G$22,868 GYD per night

Guest favorite

Home in Cudjoe Key

5.0 out of 5 average rating, 10 reviews

Sea Turtle Cove

Jun 23 – 30

G$61,129 GYD per night

Superhost

Tiny home in Big Pine Key

4.84 out of 5 average rating, 31 reviews

Tiny Fish Haus

Feb 23 – Mar 2

G$67,687 GYD per night

Superhost

Cottage in Cudjoe Key

4.91 out of 5 average rating, 53 reviews

Turtle Cove Views @ Venture Out - Waterfront

Jun 15 – 22

G$114,286 GYD per night

Superhost

Home in Cudjoe Key

4.84 out of 5 average rating, 37 reviews

Keys Cove

Apr 20 – 27

G$84,129 GYD per night

Superhost

Home in Cudjoe Key

4.87 out of 5 average rating, 70 reviews

Island Oasis ~ YOUR Paradise Awaits!

Mar 30 – Apr 6

G$70,851 GYD per night

Show all

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$22,989 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 cottage rentals in Summerland Key?
Experience the best of Summerland Key with our cottage rentals, starting at about $170 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.

Summerland Key vacation rentals

Top-rated vacation rentals in Summerland Key

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Summerland Key vacation rentals

Stay near Summerland Key's top sights

Other great vacation rentals in Summerland Key

Camper/RV in Big Pine Key

Camper/RV in Big Pine Key

Home in Cudjoe Key

Home in Cudjoe Key

Cottage in Cudjoe Key

Home in Cudjoe Key

Home in Cudjoe Key

Home in Cudjoe Key

Other great vacation rentals in Summerland Key

Home in Cudjoe Key

Vacation home in Cudjoe Key

Campsite in Cudjoe Key

Home in Cudjoe Key

Tiny home in Big Pine Key

Cottage in Cudjoe Key

Home in Cudjoe Key

Home in Cudjoe Key

Quick stats about vacation rentals in Summerland Key

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Summerland Key?

Are there pet-friendly vacation rentals in Summerland Key?

How much does it cost to stay in cottage rentals in Summerland Key?

Do house rentals in Summerland Key have self check-in?

Are there Summerland Key house rentals on Airbnb with pools?

Do house rentals in Summerland Key have a bbq area?

Do cottage rentals in Summerland Key have wifi?

Are there family-friendly house rentals in Summerland Key?

Destinations to explore